cheminform abstract: diastereoselective acyclic aza-(2,3) wittig sigmatropic rearrangements
TRANSCRIPT
1997 amines
amines (benzene compounds)Q 0120
42 - 104Diastereoselective Acyclic Aza-(2,3) Wittig Sigmatropic Rearrange-ments. — The title reaction proceeds with complete diastereoselectivitywhen a dimethylphenylsilane group is incorporated at the C-2 position. Withother groups attached at the C-2 position such as phenyl, thiophenyl thediastereoselectivity is decreased. Compounds with sulfoxide and sulfone sub-stituent (cf. (VIII) and (X)) do not undergo the Wittig rearrangement under thedescribed conditions. The reaction mechanism is discussed. — (ANDERSON,J. C.; SMITH, S. C.; SWARBRICK, M. E.; J. Chem. Soc., Perkin Trans.1 (1997) 10, 1517-1521; Dep. Chem., Univ. Sheffield, Sheffield S3 7HF, UK; EN)
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