Concepedia

Sulfinyl Group as an Intramolecular Nucleophile:  Synthesis of Bromohydrins from β-Methyl-γ,δ-unsaturated Sulfoxides with High 1,2-Asymmetric Induction

Sadagopan Raghavan, S. Ramakrishna Reddy, Kurissery A. Tony, Ch. Naveen Kumar, Ashok K. Varma, Ashwini Nangia

The Journal of Organic Chemistry · 2002 · 34 citations · 7 references

DOI

Concepts

Abstract

Bromohydrins have been prepared from beta-methyl-gamma,delta-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 (18)O labeling study and X-ray crystallography.

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