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Phosphahelicenes in Asymmetric Organocatalysis: [3+2] Cyclizations of γ‐Substituted Allenes and Electron‐Poor Olefins
Author(s) -
Gicquel Maxime,
Zhang Yang,
Aillard Paul,
Retailleau Pascal,
Voituriez Arnaud,
Marinetti Angela
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500299
Subject(s) - enantioselective synthesis , organocatalysis , cyclopentene , chemistry , enantiomer , organic chemistry , combinatorial chemistry , catalysis
The first use of phosphahelicene in enantioselective organocatalysis is reported. New chiral phosphahelicenes have been prepared and enable highly enantioselective [3+2] cyclization reactions between arylidene‐ or alkylidenemalononitriles and γ‐substituted allenoates or cyanoallenes. These reactions afford cyclopentene derivatives in both high yields and diastereoselectivities, with enantiomeric excesses of up to 97 %.