Facile Synthesis of Enantiopure Sugar Alcohols: Asymmetric Hydrogenation and Dynamic Kinetic Resolution Combined

Wang, Jiang1,3; Shao, Pan-Lin2,3; Lin, Xin2; Ma, Baode2,3; Wen, Jialin3,4; Zhang, Xumu3

2020-08-18

10.1002/anie.202006661

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

An unprecedented Ir/f-amphox-catalyzed asymmetric hydrogenation of racemic 2,3-syn-dihydroxy-1,4-diones is presented involving dynamic kinetic resolution, which produces (1R,2R,3R,4R)-tetraols. This protocol constitutes an efficient and straightforward approach to accessing sugar alcohols bearing four contiguous stereocenters. The strategy exhibits various advantages over existing methods, including excellent yields (up to 98 %), exceptional stereoselectivities (up to 99:1 dr, 99.9 %ee), operational simplicity and substrate generality. Moreover, the nature of the reaction was revealed as a stepwise transformation by in situ Fourier-transform infrared spectroscopy and isolation of intermediates.

1 2 3 4-tetraols chirality dynamic kinetic resolution iridium sugar alcohols

SCI ; EI ; IC ; CCR

英语

NI论文

通讯

Science, Technology and Innovation Commission of Shenzhen[JCYJ20190809160211372][KQTD20150717103157174] ; National Natural Science Foundation of China[21991113] ; Shenzhen Clean Energy Research Institute[CERI-KY-2019-003] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Multidisciplinary

WOS:000560288800001

WILEY-V C H VERLAG GMBH

20203409081461

Kinetics ; Hydrogenation ; Fourier transform infrared spectroscopy ; Reaction intermediates

Precious Metals:547.1 ; Fluid Flow, General:631.1 ; Chemistry:801 ; Chemical Reactions:802.2 ; Chemical Products Generally:804 ; Classical Physics; Quantum Theory; Relativity:931

CHEMISTRY

Web of Science

1.Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Coll Innovat & Entrepreneurship, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Dept Chem, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China
4.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China

Wang, Jiang,Shao, Pan-Lin,Lin, Xin,et al. Facile Synthesis of Enantiopure Sugar Alcohols: Asymmetric Hydrogenation and Dynamic Kinetic Resolution Combined[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020,59(41):18166-18171.

Wang, Jiang,Shao, Pan-Lin,Lin, Xin,Ma, Baode,Wen, Jialin,&Zhang, Xumu.(2020).Facile Synthesis of Enantiopure Sugar Alcohols: Asymmetric Hydrogenation and Dynamic Kinetic Resolution Combined.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,59(41),18166-18171.

Wang, Jiang,et al."Facile Synthesis of Enantiopure Sugar Alcohols: Asymmetric Hydrogenation and Dynamic Kinetic Resolution Combined".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59.41(2020):18166-18171.