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Issue 20, 1998
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Preparation of enantiomerically enriched bromohydrins from [N-( p-tolylsulfonyl)sulfoximino]oxiranes using in situ reduction of α-bromo aldehydes

Abstract

Treatment of enantiomerically pure [N-( p-tolylsulfonyl)sulfoximino]oxiranes 6 with MgBr2 in the presence of tetrabutylammonium borohydride gives enantiomerically enriched bromohydrins 3, together with small amounts of the primary alcohols 11. The bromohydrins 3 are isolated in good yields with enantiomeric excesses in the range 70% to 91%. This process establishes that α-bromo aldehydes have sufficient configurational stability to be viable synthetic intermediates.

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Article type: Paper
DOI: 10.1039/A805839C
J. Chem. Soc., Perkin Trans. 1, 1998, 3359-3364

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    Preparation of enantiomerically enriched bromohydrins from [N-( p-tolylsulfonyl)sulfoximino]oxiranes using in situ reduction of α-bromo aldehydes

    P. L. Bailey, A. D. Briggs, R. F. W. Jackson and J. Pietruszka, J. Chem. Soc., Perkin Trans. 1, 1998, 3359
    DOI: 10.1039/A805839C

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