Issue 83, 2021

Efficient asymmetric syntheses of α-quaternary lactones and esters through chiral bifunctional sulfide-catalyzed desymmetrizing bromolactonization of α,α-diallyl carboxylic acids

Abstract

Asymmetric halolactonizations are powerful methods for the syntheses of chiral lactones. Catalytic and highly enantioselective halolactonizations of α-allyl carboxylic acids, however, continue to present a formidable challenge. Herein, we report the chiral bifunctional sulfide-catalyzed desymmetrizing bromolactonizations of α,α-diallyl carboxylic acids. These reactions efficiently produced chiral α-quaternary lactones and esters.

Graphical abstract: Efficient asymmetric syntheses of α-quaternary lactones and esters through chiral bifunctional sulfide-catalyzed desymmetrizing bromolactonization of α,α-diallyl carboxylic acids

Supplementary files

Article information

Article type
Communication
Submitted
17 Jul 2021
Accepted
22 Sep 2021
First published
23 Sep 2021

Chem. Commun., 2021,57, 10907-10910

Efficient asymmetric syntheses of α-quaternary lactones and esters through chiral bifunctional sulfide-catalyzed desymmetrizing bromolactonization of α,α-diallyl carboxylic acids

M. Hiraki, K. Okuno, R. Nishiyori, A. A. Noser and S. Shirakawa, Chem. Commun., 2021, 57, 10907 DOI: 10.1039/D1CC03874E

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