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Organocatalytic Sigmatropic Reactions: Development of a [2,3] Wittig Rearrangement through Secondary Amine Catalysis
Author(s) -
McNally Andrew,
Evans Brian,
Gaunt Matthew J.
Publication year - 2006
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.200504301
Subject(s) - amine gas treating , wittig reaction , sigmatropic reaction , organocatalysis , chemistry , enamine , catalysis , organic chemistry , enantioselective synthesis , combinatorial chemistry , stereochemistry
Simple secondary amine organocatalysts induce a general [2,3] Wittig rearrangement via an enamine under extremely mild conditions. The organocatalytic rearrangement gives good diastereoselectivities over a range of substrates and generates the syn isomer, which is contrary to what would be expected from the conventional [2,3]‐reaction.