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Reactions of chiral β-ketosulfoxides with Et2AlCN: Asymmetric synthesis of cyanohydrin derivatives.

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
32
Issue
27
Identifiers
DOI: 10.1016/s0040-4039(00)79720-6
Disciplines
  • Chemistry

Abstract

Abstract The reaction of chiral p-tolylsulfinylmethyl ketones (R-CO-CH2-SOTol, RPh, Et and t-Bu) with Et2AlCN, yields almost optically pure sulfinyl cyanohydrins (d.e. ≥ 96%). The reaction was quicker in the presence of ZnCl2, but the stereochemical results were identical, The cyanohydrins were transformed into the α-methyl α-hydroxyamides (e.e.-92%) by hydrolysis of the CN group and subsequent hydrogenolysis of the CS bond.

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