Journal
TETRAHEDRON
Volume 66, Issue 33, Pages 6300-6308Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.04.095
Keywords
5-endo-trig; Cyclisation; Aza-[2,3]-Wittig; Proline; Sigmatropic rearrangement; Vinyl silane
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The major diastereoisomers of aza-[2,3]-Wittig sigmatropic rearrangement products from alpha-amino acid derivatives are susceptible to a rare nucleophilic 5-endo-trig cyclisations of an amine onto a non-conjugated vinylsilane in high yield and complete diastereocontrol. Five examples are presented, with cyclisation yields between 35 and 87%. A rationale for the stereoselectivity of the cyclisation is forwarded based upon the steric control factors that have been documented for the aza-[2,3]-Wittig sigmatropic rearrangement. A discussion of the mechanism in the context of the reaction conditions is also presented. Oxidation of the silyl group to a hydroxyl group and complete removal were demonstrated for synthetic utility. (C) 2010 Elsevier Ltd. All rights reserved.
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