Sulfinyl group as an intramolecular nucleophile: Synthesis of bromohydrins from β-methyl-γ,δ-unsaturated sulfoxides with high 1,2-asymmetric induction
Sulfinyl group as an intramolecular nucleophile: Synthesis of bromohydrins from β-methyl-γ,δ-unsaturated sulfoxides with high 1,2-asymmetric induction
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Date
2002-08-09
Authors
Raghavan, Sadagopan
Reddy, S. Ramakrishna
Tony, K. A.
Kumar, Ch Naveen
Varma, Ashok K.
Nangia, Ashwini
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Abstract
Bromohydrins have been prepared from β-methyl-γ,δ-unsaturated sulfoxides with high regio- and stereoselectivity. The reaction proceeds via neighboring group participation of the sulfinyl moiety with inversion of sulfoxide configuration as proven by an 18O labeling study and x-ray crystallography.
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Journal of Organic Chemistry. v.67(16)