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Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile ?-Keto Esters.

ABSTRACT: Enantioconvergent arylation reactions of boronic acids and racemic ?-stereogenic ?-keto esters have been developed. The reactions are catalyzed by a chiral (diene)Rh(I) complex and provide a wide array of ?-stereogenic tertiary aryl glycolate derivatives with high levels of diastereo- and enantioselectivity. Racemization studies employing a series of sterically differentiated tertiary amines suggest that the steric nature of the amine base additive exerts a significant influence on the rate of substrate racemization.

SUBMITTER: Bartlett SL

PROVIDER: S-EPMC5352479 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters.

Bartlett Samuel L SL Keiter Kimberly M KM Johnson Jeffrey S JS

Journal of the American Chemical Society 20170302 10

Enantioconvergent arylation reactions of boronic acids and racemic β-stereogenic α-keto esters have been developed. The reactions are catalyzed by a chiral (diene)Rh(I) complex and provide a wide array of β-stereogenic tertiary aryl glycolate derivatives with high levels of diastereo- and enantioselectivity. Racemization studies employing a series of sterically differentiated tertiary amines suggest that the steric nature of the amine base additive exerts a significant influence on the rate of s ...[more]

PMID: 28252953

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