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

Chem Commun (Camb)

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

Published: October 2021

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.

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Source
http://dx.doi.org/10.1039/d1cc03874eDOI Listing

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