Differentiating the Allyl and Propargyl Groups on α‐Quaternary Carboxylic Acids via Chiral Bifunctional Sulfide‐Catalyzed Kinetic Resolution

Author:

Okuno Ken1,Chan Bun2,Shirakawa Seiji1ORCID

Affiliation:

1. Department of Environmental Science Graduate School of Fisheries and Environmental Sciences Nagasaki University 1-14 Bunkyo-machi Nagasaki 852-8521 Japan

2. Graduate School of Engineering Nagasaki University 1-14 Bunkyo-machi Nagasaki 852-8521 Japan

Abstract

AbstractCatalytic kinetic resolution of racemic organic compounds is a reliable method to enantioselectively prepare important chiral molecules. Substrates for the kinetic resolution, however, generally required significantly different substituents at a chiral center. Catalytic kinetic resolution of racemic molecules possessing two similar substituents at a chiral center has remained a formidable challenge. In this context, we became interested in the catalytic kinetic resolution of racemic compounds bearing both allyl and propargyl groups, which are similar but useful substituents, at a chiral center. Herein, we report a kinetic resolution of α‐allyl‐α‐propargyl carboxylic acids bearing an all‐carbon quaternary stereocenter via chiral bifunctional sulfide‐catalyzed bromolactonization. The synthetic utility of the resultant optically active compounds obtained via kinetic resolution was also demonstrated.magnified image

Funder

Kumagai Foundation for Science and Technology

Naohiko Fukuoka Memorial Foundation

Nagasaki University

Publisher

Wiley

Subject

General Chemistry

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