Issue 14, 1993

Recoverable chiral sulfoxides for asymmetric synthesis: preparation, regeneration and application to the asymmetric aldol reaction

Abstract

The synthesis of a novel source of chiral sulfoxide and its application to the control of asymmetric aldol reactions is described. The sulfoxide precursor S(s)R-(+)-cis-4 may be recycled and thus affords a considerable advantage over currently available methodology. Studies of the origin of the stereochemical outcome of the aldol reactions of the derived enolate S(s)R-(–)-10b reveal that it is the result of thermodynamic, not kinetic, control.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 1581-1589

Recoverable chiral sulfoxides for asymmetric synthesis: preparation, regeneration and application to the asymmetric aldol reaction

R. J. Butlin, I. D. Linney, D. J. Critcher, M. F. Mahon, K. C. Molloy and M. Wills, J. Chem. Soc., Perkin Trans. 1, 1993, 1581 DOI: 10.1039/P19930001581

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