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Exploiting Organocatalysis: Enantioselective Synthesis of Vinyl Glycines by Allylic Sulfimide [2,3] Sigmatropic Rearrangement
Author(s) -
Armstrong Alan,
Challinor Lee,
Moir Jennifer H.
Publication year - 2007
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.200701459
Subject(s) - enantioselective synthesis , sigmatropic reaction , organocatalysis , allylic rearrangement , chemistry , organic chemistry , catalysis
Have it both ways : Enantiomerically enriched E vinyl glycines may be accessed from aldehydes in a concise sequence that combines an organocatalytic α sulfenylation, stereoselective olefination, a sulfimidation, and a [2,3] sigmatropic rearrangement (see scheme, Boc= tert ‐butoxycarbonyl, n Hex= n ‐hexyl). Either enantiomeric series can be accessed by control of the alkene geometry in the olefination step.