Asymmetric Dihydroxylation-Based Kinetic Resolution of Allylic Amides Enabled by Noncovalent p-Interactions

Li, Chengcheng1,2,3; Chen, Fumin1,2,3; Mu, Qianqian1,2; Xu, Chen1,2

2022-11-01

10.1021/acs.orglett.2c03486

ORGANIC LETTERS   Impact Factor & Quartile

1523-7060

1523-7052

While Sharpless asymmetric dihydroxylation is widely utilized to convert various alkenes into diols with excellent enantioselectivies, kinetic resolution by means of this fundamental catalysis has generally proven to be ineffective. Here we report that, by relying on noncovalent pi-interactions that purposely include the substrate's stereocenter in the corresponding catalyst- substrate interaction framework, AD-based kinetic resolution of allylic amides is realized. This method enables such versatile chiral building blocks to be easily accessed with excellent enantiomeric excesses (ee's).

SCI

English

NI Journal Papers

First ; Corresponding

[C17783101] ; [2020B121201002] ; [K21211026] ; [KQTD20180411143514543] ; [K20215006]

Chemistry

Chemistry, Organic

WOS:000893251600001

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
3.Harbin Inst Technol, Sch Chem & Chem Engn, Harbin 150001, Peoples R China

Li, Chengcheng,Chen, Fumin,Mu, Qianqian,et al. Asymmetric Dihydroxylation-Based Kinetic Resolution of Allylic Amides Enabled by Noncovalent p-Interactions[J]. ORGANIC LETTERS,2022.

Li, Chengcheng,Chen, Fumin,Mu, Qianqian,&Xu, Chen.(2022).Asymmetric Dihydroxylation-Based Kinetic Resolution of Allylic Amides Enabled by Noncovalent p-Interactions.ORGANIC LETTERS.

Li, Chengcheng,et al."Asymmetric Dihydroxylation-Based Kinetic Resolution of Allylic Amides Enabled by Noncovalent p-Interactions".ORGANIC LETTERS (2022).