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Organocatalytic, Highly Enantioselective Vinylogous Mukaiyama–Michael Reaction of Acyclic Dienol Silyl Ethers
Author(s) -
Gupta Vaishali,
Sudhir Sai,
Mandal Tanmay,
Schneider Christoph
Publication year - 2012
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.201207058
Subject(s) - enantioselective synthesis , silylation , stereocenter , iminium , michael reaction , chemistry , organic chemistry , catalysis
Now also acyclic : The first catalytic, enantioselective, vinylogous Michael reaction of linear, acyclic dienol silyl ethers was achieved. The reaction, based upon the principle of iminium ion catalysis, delivered 1,7‐dioxo compounds in one step with good yields, complete regio‐, and excellent enantioselectivity. γ‐Substituted dienol silyl ethers furnished products with two new stereogenic centers with good diastereoselectivity. Ms=mesityl, PNBA= para ‐nitrobenzoic acid.