[1] RENZI P. Organocatalytic synthesis of axially chiral atropisomers[J]. Organic & Biomolecular Chemistry, 2017, 15(21): 4506-4516.
[2] YAMANAKA K, RYAN K S, GULDER T A, et al. Flavoenzyme-catalyzed atropo-selective N,C-bipyrrole homocoupling in marinopyrrole biosynthesis[J]. Journal of the American Chemical Society, 2012, 134(30): 12434-12437.
[3] BRINGMANN G, GULDER T, GULDER T A M, et al. Atroposelective total synthesis of axially chiral biaryl natural products[J]. Chemical Reviews, 2011, 111(2): 563-639.
[4] BRINGMANN G, MENCHE D. Stereoselective total synthesis of axially chiral natural products via biaryl lactones[J]. Accounts of Chemical Research, 2001, 34(8): 615-624.
[5] COLLINS B S L, KISTEMAKER J C M, OTTEN E, et al. A chemically powered unidirectional rotary molecular motor based on a palladium redox cycle[J]. Nature Chemistry, 2016, 8(9): 860-866.
[6] SAPOTTA M, SPENST P, SAHA-MöLLER C R, et al. Guest-mediated chirality transfer in the host–guest complexes of an atropisomeric perylene bisimide cyclophane host[J]. Organic Chemistry Frontiers, 2019, 6(7): 892-899.
[7] CHENG J K, XIANG S H, LI S, et al. Recent advances in catalytic asymmetric construction of atropisomers[J]. Chemical Reviews, 2021, 121(8): 4805-4902.
[8] WANG Y B, TAN B. Construction of axially chiral compounds via asymmetric organocatalysis[J]. Accounts of Chemical Research, 2018, 51(2): 534-547.
[9] MIYASHITA A, YASUDA A, TAKAYA H, et al. Synthesis of 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of α-(acylamino)acrylic acids[J]. Journal of the American Chemical Society, 1980, 102(27): 7932–7934.
[10] AKIYAMA T, ITOH J, YOKOTA K, et al. Enantioselective mannich-type reaction catalyzed by a chiral Brønsted acid[J]. Angewandte Chemie International Edition, 2004, 43(12): 1566-1568.
[11] URAGUCHI D, TERADA M. Chiral Brønsted acid-catalyzed direct mannich reactions via electrophilic activation[J]. Journal of the American Chemical Society, 2004, 126(17): 5356–5357.
[12] NAKASHIMA D, YAMAMOTO H. Design of chiral N-triflyl phosphoramide as a strong chiral Brønsted acid and its application to asymmetric Diels-Alder reaction[J]. Journal of the American Chemical Society, 2006, 126(17): 5356–5357.
[13] PENG B, MA J, GUO J, et al. A powerful chiral super Brønsted C-H acid for asymmetric catalysis[J]. Journal of the American Chemical Society, 2022, 144(7): 2853-2860.66参考文献
[14] XU L W, LI L, LAI G Q, et al. The recent synthesis and application of silicon-stereogenic silanes: A renewed and significant challenge in asymmetric synthesis[J]. Chemical Society Reviews, 2011, 40: 1777-1790.
[15] BEEMELMANNS C, HUSMANN R, WHELLIGAN D K, et al. Planar-chiral bis-silanols and diols as H-bonding asymmetric organocatalysts[J]. European Journal of Organic Chemistry, 2012, (18): 3373-3376.
[16] SCHAFER A G, WIETING J M, FISHER T J, et al. Chiral silanediols in anion -binding catalysis[J]. Angewandte Chemie International Edition, 2013, 52: 11321-11324.
[17] GE Y, HUANG X, KE J, et al. Transition-metal-catalyzed enantioselective C-H silylation[J]. Chem Catalysis, 2022, 2: 2898-2928.
[18] SHINTANI R. Recent progress in catalytic enantioselective desymmetrization of prochiral organosilanes for the synthesis of silicon-stereogenic compounds[J]. Synlett, 2017, 29(04): 388-396.
[19] AHRENDT K A, BORTHS C J, MACMILLAN D W C. New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction[J]. Journal of the American Chemical Society, 2000, 122(17): 4243–4244.
[20] REYES E, PRIETO L, MILELLI A. Asymmetric organocatalysis: A survival guide to medicinal chemists[J]. Molecules, 2022, 28(1).
[21] YANG H, YANG X, TANG W. Transition-metal catalyzed asymmetric carbon–carbon crosscoupling with chiral ligands[J]. Tetrahedron, 2016, 72(41): 6143-6174.
[22] TANAKA K. Transition-metal-catalyzed enantioselective
[2+2+2] cycloadditions for the synthesis of axially chiral biaryls[J]. Chemistry-A Asian Journal, 2009, 4(4): 508-518.
[23] LIAO G, ZHANG T, LIN Z K, et al. Transition metal-catalyzed enantioselective C-Hfunctionalization via chiral transient directing group strategies[J]. Angewandte Chemie International Edition, 2020, 59(45): 19773-19786.
[24] LIU C X, ZHANG W W, YIN S Y, et al. Synthesis of atropisomers by transition-metalcatalyzed asymmetric C-H functionalization reactions[J]. Journal of the American Chemical Society, 2021, 143(35): 14025-14040.
[25] ZHANG X, ZHAO K, GU Z. Transition metal-catalyzed biaryl atropisomer synthesis via a torsional strain promoted ring-opening reaction[J]. Accounts of Chemical Research, 2022, 55(12): 1620-1633.
[26] WENCEL-DELORD J, PANOSSIAN A, LEROUX F R, et al. Recent advances and new concepts for the synthesis of axially stereoenriched biaryls[J]. Chemical Society Reviews, 2015, 44(11): 3418-3430.
[27] LI G Q, GAO H, KEENE C, et al. Organocatalytic aryl-aryl bond formation: An atroposelective
[3,3]-rearrangement approach to BINAM derivatives[J]. Journal of the American Chemical Society, 2013, 135(20): 7414-7417.
[28] DE C K, PESCIAIOLI F, LIST B. Catalytic asymmetric benzidine rearrangement[J]. Angewandte Chemie International Edition, 2013, 52(35): 9293-9295.67参考文献
[29] CHEN Y H, CHENG D J, ZHANG J, et al. Atroposelective synthesis of axially chiral biaryldiols via organocatalytic arylation of 2-naphthols[J]. Journal of the American Chemical Society, 2015, 137(48): 15062-15065.
[30] MOLITERNO M, CARI R, PUGLISI A, et al. Quinine-catalyzed asymmetric synthesis of 2,2'-binaphthol-type biaryls under mild reaction conditions[J]. Angewandte Chemie International Edition, 2016, 55(22): 6525-6529.
[31] COOMBS G, SAK M H, MILLER S J. Peptide-catalyzed fragment couplings that form axially chiral non-C2-symmetric biaryls[J]. Angewandte Chemie International Edition, 2020, 59(7): 2875-2880.
[32] WANG J Z, ZHOU J, XU C, et al. Symmetry in cascade chirality-transfer processes: A catalytic atroposelective direct arylation approach to BINOL derivatives[J]. Journal of the American Chemical Society, 2016, 138(16): 5202-5205.
[33] CHEN Y H, QI L W, FANG F, et al. Organocatalytic atroposelective arylation of 2 -naphthylamines as a practical approach to axially chiral biaryl amino alcohols[J]. Angewandte Chemie International Edition, 2017, 56(51): 16308-16312.
[34] LINK A, SPARR C. Organocatalytic atroposelective aldol condensation: Synthesis of axially chiral biaryls by arene formation[J]. Angewandte Chemie International Edition, 2014, 53(21): 5458-5461.
[35] LOTTER D, NEUBURGER M, RICKHAUS M, et al. Stereoselective arene -forming aldol condensation: Synthesis of configurationally stable oligo-1,2-naphthylenes[J]. Angewandte Chemie International Edition, 2016, 55(8): 2920-2923.
[36] WITZIG R M, FäSEKE V C, HäUSSINGER D, et al. Atroposelective synthesis of tetra -ortho-substituted biaryls by catalyst-controlled non-canonical polyketide cyclizations[J]. Nature Catalysis, 2019, 2(10): 925-930.
[37] GUSTAFSON J L, LIM D, MILLER S J. Dynamic kinetic resolution of biaryl atropisomers via peptide-catalyzed asymmetric bromination[J]. Science, 2010, 328(5983): 1251 -1255.
[38] SHIRAKAWA S, WU X, MARUOKA K. Kinetic resolution of axially chiral 2-amino-1,1'-biaryls by phase-transfer-catalyzed N-allylation[J]. Angewandte Chemie International Edition, 2013, 52(52): 14200-14203.
[39] CHENG D J, YAN L, TIAN S K, et al. Highly enantioselective kinetic resolution of axially chiral BINAM derivatives catalyzed by a Brønsted acid[J]. Angewandte Chemie International Edition, 2014, 53(14): 3684-3687.
[40] LU S, POH S B, ZHAO Y. Kinetic resolution of 1,1'-biaryl-2,2'-diols and amino alcohols through NHC-catalyzed atroposelective acylation[J]. Angewandte Chemie International Edition, 2014, 53(41): 11041-11045.
[41] YANG G, GUO D, MENG D, et al. NHC-catalyzed atropoenantioselective synthesis of axially chiral biaryl amino alcohols via a cooperative strategy[J]. Nature Communications, 2019, 10(1): 3062.68参考文献
[42] LU S, POH S B, RONG Z Q, et al. NHC-catalyzed atroposelective acylation of phenols: Access to enantiopure NOBIN analogs by desymmetrization[J]. Organic Letters, 2019, 21(15): 6169-6172.
[43] BRINGMANN G, WALTER R, WEIRICH R. The directed synthesis of biaryl compounds: Modern concepts and strategies[J]. Angewandte Chemie International Edition, 1990, 29(9): 977-991.
[44] YU C, HUANG H, LI X, et al. Dynamic kinetic resolution of biaryl lactones v ia a chiral bifunctional amine thiourea-catalyzed highly atropo-enantioselective transesterification[J]. Journal of the American Chemical Society, 2016, 138(22): 6956-6959.
[45] WANG G, SHI Q, HU W, et al. Organocatalytic asymmetric N-sulfonyl amide C-N bond activation to access axially chiral biaryl amino acids[J]. Nature Communications, 2020, 11(1): 946-954.
[46] CORRIU R J P, MOREAU J J E. Synthese asymetrique d'alcoxysilanes catalysee par des complexes du rhodium[J]. Tetrahedron Letters, 1973, 14(45): 4469-4472.
[47] OHTA T, ITO M, TSUNETO A, et al. Asymmetric synthesis of silanes with a stereogenic centre at silicon via hydrosilylation of symmetric ketones with prochiral diaryl silanes catalysed by BINAP–RhI complexes[J]. Journal of the Chemical Society, Chemical Communications,, 1994: 2525-2526.
[48] ZHU J, CHEN S, HE C. Catalytic enantioselective dehydrogenative Si-O coupling to access chiroptical silicon-stereogenic siloxanes and alkoxysilanes[J]. Journal of the American Chemical Society, 2021, 143(14): 5301-5307.
[49] YANG W, LIU L, GUO J, et al. Enantioselective hydroxylation of dihydrosilanes to Sichiral silanols catalyzed by in situ generated copper(II) species[J]. Angewandte Chemie International Edition, 2022, 61(32): e202205743.
[50] TAMAO K N, K. HIROYUKI, I. YAMAGUCHI, S. SHIRO, M. Axially chiral spirosilanes via catalytic asymmetric intramolecular hydrosilation[J]. Journal of the American Chemical Society, 1996, 118: 12469-12470.
[51] CHANG X, MA P L, CHEN H C, et al. Asymmetric synthesis and application of chiral spirosilabiindanes[J]. Angewandte Chemie International Edition, 2020, 59(23): 8937-8940.
[52] HUANG Y H, WU Y, ZHU Z, et al. Enantioselective synthesis of silicon-stereogenic monohydrosilanes by rhodium-catalyzed intramolecular hydrosilylation[J]. Angewandte Chemie International Edition, 2022, 61(1): e202113052.
[53] ZHAN G, TENG H L, LUO Y, et al. Enantioselective construction of silicon -stereogenic silanes by scandium-catalyzed intermolecular alkene hydrosilylation[J]. Angewandte Chemie International Edition, 2018, 57(38): 12342-12346.
[54] MU D, YUAN W, CHEN S, et al. Streamlined construction of silicon-stereogenic silanes by tandem enantioselective C-H silylation/alkene hydrosilylation[J]. Journal of the American Chemical Society, 2020, 142(31): 13459-13468.69参考文献
[55] YANG B, YANG W, GUO Y, et al. Enantioselective silylation of aliphatic C-H bonds for the synthesis of silicon-stereogenic dihydrobenzosiloles[J]. Angewandte Chemie International Edition, 2020, 59(49): 22217-22222.
[56] GUO Y, LIU M M, ZHU X, et al. Catalytic asymmetric synthesis of silicon -stereogenic dihydrodibenzosilines: Silicon central-to-axial chirality relay[J]. Angewandte Chemie International Edition, 2021, 60(25): 13887-13891.
[57] YASUTOMI Y, SUEMATSU H, KATSUKI T. Iridium(III)-catalyzed enantioselective Si−Hbond insertion and formation of an enantioenriched silicon center[J]. Journal of the American Chemical Society, 2010, 132: 4510-4511.
[58] IGAWA K, YOSHIHIRO D, ICHIKAWA N, et al. Catalytic enantioselective synthesis of alkenylhydrosilanes[J]. Angewandte Chemie International Edition, 2012, 51(51): 12745-12748.
[59] WEN H, WAN X, HUANG Z. Asymmetric synthesis of silicon-stereogenic vinylhydrosilanes by cobalt-catalyzed regio- and enantioselective alkyne hydrosilylation with dihydrosilanes[J]. Angewandte Chemie International Edition, 2018, 57(21): 6319-6323.
[60] KURIHARA Y, NISHIKAWA M, YAMANOI Y, et al. Synthesis of optically active tertiary silanes via Pd-catalyzed enantioselective arylation of secondary silanes[J]. Chemical Communications, 2012, 48(94): 11564-11566.
[61] CHEN L, HUANG J B, XU Z, et al. Palladium-catalyzed Si–C bond-forming silylation of aryl iodides with hydrosilanes: An enhanced enantioselective synthesis of silicon -stereogenic silanes by desymmetrization[J]. RSC Advances, 2016, 6(71): 67113-67117.
[62] KUNINOBU Y, YAMAUCHI K, TAMURA N, et al. Rhodium-catalyzed asymmetric synthesis of spirosilabifluorene derivatives[J]. Angewandte Chemie International Edition, 2013, 52(5): 1520-1522.
[63] MA W, LIU L C, AN K, et al. Rhodium-catalyzed synthesis of chiral monohydrosilanes by intramolecular C-H functionalization of dihydrosilanes[J]. Angewandte Chemie International Edition, 2021, 60(8): 4245-4251.
[64] ZENG Y, FANG X J, TANG R H, et al. Rhodium-catalyzed dynamic kinetic asymmetric hydrosilylation to access silicon-stereogenic center[J]. Angewandte Chemie International Edition, 2022, 61(51): e202214147.
[65] SHINTANI R, MORIYA K, HAYASHI T. Palladium-catalyzed enantioselective desymmetrization of silacyclobutanes: Construction of silacycles possessing a tetraorganosilicon stereocenter[J]. Journal of the American Chemical Society, 2011, 133(41): 16440-16443.
[66] SHINTANI R, MORIYA K, HAYASHI T. Palladium-catalyzed desymmetrization of silacyclobutanes with alkynes: Enantioselective synthesis of silicon-stereogenic 1-sila-2-cyclohexenes and mechanistic considerations[J]. Organic Letters, 2012, 14: 2902-2905.70参考文献
[67] CHEN H, CHEN Y, TANG X, et al. Rhodium-catalyzed reaction of silacyclobutanes with unactivated alkynes to afford silacyclohexenes[J]. Angewandte Chemie International Edition, 2019, 58(14): 4695-4699.
[68] ZHANG Q W, AN K, LIU L C, et al. Construction of chiral tetraorganosilicons by tandem desymmetrization of silacyclobutanes/intermolecular dehydrogenative silylation[J]. Angewandte Chemie International Edition, 2017, 56(4): 1125-1129.
[69] ZHANG J, YAN N, JU C W, et al. Nickel(0)-catalyzed asymmetric ring expansion toward enantioenriched silicon-stereogenic benzosiloles[J]. Angewandte Chemie International Edition, 2021, 60(49): 25723-25728.
[70] AN K, MA W, LIU L C, et al. Rhodium hydride enabled enantioselective intermolecular CH silylation to access acyclic stereogenic Si-H[J]. Nature Communications, 2022, 13(1): 847-856.
[71] SHINTANI R, MACIVER E E, TAMAKUNI F, et al. Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic dibenzooxasilines via enantioselective transmetalation[J].Journal of the American Chemical Society, 2012, 134(41): 16955-16958.
[72] ONOE M, BABA K, KIM Y, et al. Rhodium-catalyzed carbon-silicon bond activation for synthesis of benzosilole derivatives[J]. Journal of the American Chemical Society, 2012, 134(47): 19477-19488.
[73] SHINTANI R, KURATA H, NOZAKI K. Rhodium-catalyzed intramolecular alkynylsilylation of alkynes[J]. Chemical Communications, 2015, 51(57): 11378-11381.
[74] KUMAR R, HOSHIMOTO Y, YABUKI H, et al. Nickel(0)-catalyzed enantio- and diastereoselective synthesis of benzoxasiloles: Ligand-controlled switching from inter- to intramolecular aryl-transfer process[J]. Journal of the American Chemical Society, 2015, 137(36): 11838-11845.
[75] FENG J, BI X, XUE X, et al. Catalytic asymmetric C-Si bond activation via torsional strainpromoted Rh-catalyzed aryl-Narasaka acylation[J]. Nature Communications, 2020, 11(1): 4449-4460.
[76] BI X, FENG J, XUE X, et al. Construction of axial chirality and silicon -stereogenic center via Rh-catalyzed asymmetric ring-opening of silafluorenes[J]. Organic Letters, 2021, 23(8): 3201-3206.
[77] ZHOU H, HAN J T, NOTHLING N, et al. Organocatalytic asymmetric synthesis of Sistereogenic silyl ethers[J]. Journal of the American Chemical Society, 2022, 144(23): 10156-10161.
[78] ZHOU H, PROPERZI R, LEUTZSCH M, et al. Organocatalytic DYKAT of Si-stereogenic silanes[J]. Journal of the American Chemical Society, 2023, 145(9): 4994-5000.
[79] ISEKI K, NAGAI T, KOBAYASHI Y. Asymmetric trifluoromethylation of aldehydes and ketones with trifluoromethyltrimethylsilane catalyzed by chiral quaternary ammonium fluorides[J]. Tetrahedron Letters, 1994, 35(19): 3137-3138.71参考文献
[80] MIZUTA S, SHIBATA N, AKITI S, et al. Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones[J]. Organic Letters, 2007, 9(18): 3707–3710.
[81] CAO W, TAN D, LEE R, et al. Enantioselective 1,2-anionotropic rearrangement of acylsilane through a bisguanidinium silicate ion pair[J]. Journal of the American Chemical Society, 2018, 140(5): 1952-1955.
[82] DENMARK S E, CULLEN L R. Catalytic conjugate addition of acyl anion equivalents promoted by fluorodesilylation[J]. Organic Letters, 2014, 16(1): 70-73.
[83] LUO J, DENG Y, DENG T, et al. Catalytic enantioconvergent conjugate addition of organosilanes via a strategy of fluorodesilylation[J]. Journal of the American Chemical Society, 2022, 144(51): 23264-23270.
[84] CHEON C H, YAMAMOTO H. Super Brønsted acid catalysis [J]. Chemical Communications, 2011, 47(11): 3043-3056.
[85] BOTT R W, EABORN C, GREASLEY P M. Aromatic reactivity. Part XXVIII. The mechanism of acid cleavage of aryl-silicon, -germanium, -tin, and -lead bonds[J]. Journal of the Chemical Society, 1964: 4804-4806.
[86] WANG K, ZHOU J, JIANG Y, et al. Selective manganese-catalyzed oxidation of hydrosilanes to silanols under neutral reaction conditions[J]. Angewandte Chemie International Edition, 2019, 58(19): 6380-6384.
[87] LIU W, JIANG Q, YANG X. A versatile method for kinetic resolution of protecting -groupfree BINAMs and NOBINs through chiral phosphoric acid catalyzed triazane formation[J]. Angewandte Chemie International Edition, 2020, 59(52): 23598-23602.
[88] USANOV D L, YAMAMOTO H. Asymmetric nozaki-hiyama propargylation of aldehydes: Enhancement of enantioselectivity by cobalt co-catalysis[J]. Angewandte Chemie International Edition, 2010, 49(44): 8169-8172.
[89] WANG X, LI C, WANG X, et al. Metal-free etherification of aryl methyl ether derivatives by C-OMe bond cleavage [J]. Organic Letters, 2018, 20(14): 4267-4272.
[90] MOLLOY J J, SEATH C P, WEST M J, et al. Interrogating Pd(II) anion metathesis using a bifunctional chemical probe: A transmetalation switch[J]. Journal of the American Chemical Society, 2018, 140(1): 126-130.
[91] KE J, ZU B, GUO Y, et al. Hexafluoroisopropanol-enabled copper-catalyzed asymmetric halogenation of cyclic diaryliodoniums for the synthesis of axially chiral 2,2'-dihalobiaryls[J]. Organic Letters, 2021, 23(2): 329-333.
[92] SUN X, LI W, HOU G, et al. Axial chirality control by 2,4-pentanediol for the alternative synthesis of C3*-tunephos chiral diphosphine ligands and their applications in highly enantioselective ruthenium-catalyzed hydrogenation of β-keto esters[J]. Advanced Synthesis & Catalysis, 2009, 351(16): 2553-2557.72参考文献
[93] JIANG J, CHEN X, WANG J, et al. Chiral biphenylamide derivative: An efficient organocatalyst for the enantioselective synthesis of α-hydroxy phosphonates[J]. Organic & Biomolecular Chemistry, 2009, 7(21): 4355-4357.
[94] XU F, HUANG D, HAN C, et al. SPINOL-derived phosphoric acids: Synthesis and application in enantioselective Friedel-Crafts reaction of indoles with imines[J]. Journal of Organic Chemistry, 2010, 75(24): 8677-8680.
[95] LI Y P, ZHU S F, ZHOU Q L. Chiral spiro phosphoramide-catalyzed sulfa-michael addition/enantioselective protonation of exocyclic enones[J]. Organic Letters, 2019, 21(23): 9391-9395.
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