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

Chengcheng Li; Fumin Chen; Qianqian Mu; Chen Xu

doi:10.1021/acs.orglett.2c03486

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

Org Lett. 2022 Dec 9;24(48):8774-8779. doi: 10.1021/acs.orglett.2c03486. Epub 2022 Nov 28.

Authors

Chengcheng Li^{1

2}, Fumin Chen^{1

2}, Qianqian Mu², Chen Xu²

Affiliations

¹ School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China.
² Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China.

PMID: 36441523
DOI: 10.1021/acs.orglett.2c03486

Abstract

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 π-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).