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Cooperative Organocatalysis for the Asymmetric γ Alkylation of α‐Branched Enals
Author(s) -
Bergonzini Giulia,
Vera Silvia,
Melchiorre Paolo
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201004761
Subject(s) - enantioselective synthesis , alkylation , organocatalysis , catalysis , chemistry , selectivity , brønsted–lowry acid–base theory , organic chemistry , combinatorial chemistry
α Branched leads to γ : The direct and enantioselective γ alkylation of α‐substituted α,β‐unsaturated aldehydes under dienamine catalysis has been achieved. A cooperative catalysis system that involves dienamine activation of α‐branched enals and chiral Brønsted acid catalysis promotes an S N 1‐alkylation pathway while ensuring complete γ‐site selectivity and high stereocontrol (see scheme; Bn=benzyl).