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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
Language(s) - German
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.200461381
Subject(s) - chemistry , sn2 reaction , stereoselectivity , allylic rearrangement , phosphine , tsuji–trost reaction , substitution (logic) , stereochemistry , catalysis , organic chemistry , computer science , programming language
Allylische Substitution metallfrei : Setzt man Acetate 1 in Gegenwart substöchiometrischer Mengen an Triphenylphosphan mit 2 um, so werden hoch diastereo‐ und regioselektiv γ‐Butenolide 3 über einen formalen Tandem‐S N 2′‐S N 2′‐Substitutionsprozess erhalten (siehe Schema).