Phosphahelicenes in Asymmetric Organocatalysis: [3+2] Cyclizations of γ‐Substituted Allenes and Electron‐Poor Olefins | Zendy

Gicquel Maxime | Zendy; Zhang Yang | Zendy; Aillard Paul | Zendy; Retailleau Pascal | Zendy; Voituriez Arnaud | Zendy; Marinetti Angela | Zendy

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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 %.

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