Efficient asymmetric syntheses of α-quaternary lactones and esters through chiral bifunctional sulfide-catalyzed desymmetrizing bromolactonization of α,α-diallyl carboxylic acids
Mana Hiraki, Ken Okuno, Ryuichi Nishiyori, Ahmed A. Noser, Seiji Shirakawa
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.
Topics & Concepts
Enantioselective synthesisBifunctionalSulfideChemistryCatalysisOrganic chemistryCarboxylic acidCombinatorial chemistryVanadium and Halogenation ChemistryOxidative Organic Chemistry ReactionsAlkaloids: synthesis and pharmacology