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Issue 24, 1993
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Application of homochiral lithium amide base chemistry to a thiane oxide system

Abstract

Treatment of the thiane oxide 6 with a homochiral lithium amide (HCLA) base 7, followed by electrophilic quench of the so-formed sulfoxide carbanion with Me3SiCl, Mel or ButCO2Et, gives the optically active products (+)-8, (+)-11 and (+)-12, respectively, in 55–60% enantiomeric excess (ee). The reaction of 6 with the HCLA base 9 can be carried out in the presence of Me3SiCl (in situ quench conditions), in which case a silylation–in situ kinetic resolution process occurs, furnishing (–)-8 in low chemical yield, in up to 69% ee. Further transformations of thiane oxides (+)-8 and (+)-11 involving reduction or removal of the ring sulfur atom were conducted, in order to establish the absolute configuration of the products. Highly stereoselective reduction of the keto sulfoxide (+)-12 was also carried out, leading ultimately to an epoxide product 20via opening of the thiane ring.

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Article type: Paper
DOI: 10.1039/P19930003099
J. Chem. Soc., Perkin Trans. 1, 1993, 3099-3104

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    Application of homochiral lithium amide base chemistry to a thiane oxide system

    R. Armer, M. J. Begley, P. J. Cox, A. Persad and N. S. Simpkins, J. Chem. Soc., Perkin Trans. 1, 1993, 3099
    DOI: 10.1039/P19930003099

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