cheminform abstract: diastereoselective acyclic aza-(2,3) wittig sigmatropic rearrangements

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1997 amines amines (benzene compounds) Q 0120 42 - 104 Diastereoselective Acyclic Aza-(2,3) Wittig Sigmatropic Rearrange- ments. The title reaction proceeds with complete diastereoselectivity when a dimethylphenylsilane group is incorporated at the C-2 position. With other groups attached at the C-2 position such as phenyl, thiophenyl the diastereoselectivity is decreased. Compounds with sulfoxide and sulfone sub- stituent (cf. (VIII) and (X)) do not undergo the Wittig rearrangement under the described 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) 1

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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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