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Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction
Author(s) -
Tap Aurélien,
Blond Aurélie,
Wakchaure Vijay N.,
List Benjamin
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201603649
Subject(s) - aldol reaction , ketene , enantioselective synthesis , chemistry , catalysis , combinatorial chemistry , organocatalysis , organic chemistry
Herein we describe the development of a catalytic enantioselective alkynylogous Mukaiyama aldol reaction. The reaction is catalyzed by a newly designed chiral disulfonimide and delivers chiral allenoates in high yields and with excellent regio‐, diastereo‐, and enantioselectivity. Our process tolerates a broad range of aldehydes in combination with diverse alkynyl‐substituted ketene acetals. The reaction products can be readily derivatized to furnish a variety of highly substituted enantiomerically enriched building blocks.