NHC-Ni(0) Catalyzed Diastereodivergent Hydroacylative Enyne Cyclization: Synthesis of Heterocycles bearing gamma-Enone

Yong, Xuefeng1,4; Ng, Elvis Wang Hei4,5; Zhen, Zibo4; Lin, Xiulian4; Gao, Weiwei4; Ho, Chun-Yu2,3,4

2020-08-24

10.1002/adsc.202000718

ADVANCED SYNTHESIS & CATALYSIS   影响因子和分区

1615-4150

1615-4169

NHC-Nickel(0) catalyzed 1,3- and 1,4-diastereodivergent hydroacylative heteroenyne cyclization with aldehydes was achieved (Syn-:Anti-, switchable from up to 1:99 to 98:2). Both sets of heterocyclic diastereomers are accessible via this route, with a high gamma-:alpha-enone structure ratio. Preliminary DFT investigations indicated that the manipulation of the N-substituent exerts a direct influence on the diastereoselectivity of NHC-nickelacyclopentene formation. The energy differences associated with the endocyclic bond angle (C-Z-C) changes noted in the calculations, might possibly account for the broad scope and high diastereodivergent selectivity observed.

Insertion Olefination Acylation Nickel Heterocycles N-heterocyclic carbenes

SCI

英语

通讯

Shenzhen Nobel Prize Scientists Laboratory Project[C17783101] ; SZ research fund[JCYJ 20170817105041557] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; SUSTech[50/Y01506014]

Chemistry

Chemistry, Applied ; Chemistry, Organic

WOS:000561913400001

WILEY-V C H VERLAG GMBH

Web of Science

1.Harbin Inst Technol, Sch Chem & Chem Engn, Harbin 150001, Heilongjiang, Peoples R China
2.Southern Univ Sci & Technol SUSTech, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China
3.Southern Univ Sci & Technol, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Guangdong, Peoples R China
4.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
5.Univ Hong Kong, Dept Chem, Pokfulam Rd, Hong Kong, Peoples R China

Yong, Xuefeng,Ng, Elvis Wang Hei,Zhen, Zibo,et al. NHC-Ni(0) Catalyzed Diastereodivergent Hydroacylative Enyne Cyclization: Synthesis of Heterocycles bearing gamma-Enone[J]. ADVANCED SYNTHESIS & CATALYSIS,2020,362(19):4164-4172.

Yong, Xuefeng,Ng, Elvis Wang Hei,Zhen, Zibo,Lin, Xiulian,Gao, Weiwei,&Ho, Chun-Yu.(2020).NHC-Ni(0) Catalyzed Diastereodivergent Hydroacylative Enyne Cyclization: Synthesis of Heterocycles bearing gamma-Enone.ADVANCED SYNTHESIS & CATALYSIS,362(19),4164-4172.

Yong, Xuefeng,et al."NHC-Ni(0) Catalyzed Diastereodivergent Hydroacylative Enyne Cyclization: Synthesis of Heterocycles bearing gamma-Enone".ADVANCED SYNTHESIS & CATALYSIS 362.19(2020):4164-4172.