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Regio‐ and Stereoselective Construction of γ‐Butenolides through Phosphine‐Catalyzed Substitution of Morita–Baylis–Hillman Acetates: An Organocatalytic Allylic Alkylation
Author(s) -
Cho ChangWoo,
Krische Michael J.
Publication year - 2004
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.200461381
Subject(s) - regioselectivity , stereoselectivity , allylic rearrangement , sn2 reaction , chemistry , substitution (logic) , tsuji–trost reaction , phosphine , substitution reaction , stereochemistry , organic chemistry , medicinal chemistry , catalysis , computer science , programming language
Hold the metal : Upon exposure of acetates 1 to substoichiometric quantities of triphenylphosphane in the presence of 2 , regioselective metal‐free allylic substitution occurs through a formal tandem S N 2′–S N 2′ substitution mechanism to provide γ‐butenolides 3 with high levels of regio‐ and diastereocontrol (see scheme).