Premium
Copper‐Catalyzed Enantioselective Construction of Tertiary Propargylic Sulfones
Author(s) -
Gómez José Enrique,
Cristòfol Àlex,
Kleij Arjan W.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814242
Subject(s) - stereocenter , enantioselective synthesis , chemistry , catalysis , functional group , combinatorial chemistry , copper , organic chemistry , polymer
Abstract Tertiary propargylic sulfones are of significant importance in organic synthesis and medicinal chemistry, but to date no general asymmetric synthesis approach has been developed. We disclose a versatile copper‐catalyzed sulfonylation of propargylic cyclic carbonates using sodium sulfinates that allows the construction of propargylic sulfones featuring elusive quaternary stereocenters. This method provides the first successful example of such an enantioselective propargylic sulfonylation, features high asymmetric induction, wide functional group tolerance, and scalability, and enables attractive product diversification.