(R)-(+)-Phenyl (p-Toluenesulfinyl)acetate

[75340-59-9]  · C15H14O3S  · (R)-(+)-Phenyl (p-Toluenesulfinyl)acetate  · (MW 274.36)

(asymmetric aldol-type condensations1)

Physical Data: [a]D +87° (CHCl3, c 0.95).

Preparative Methods: conveniently prepared by deprotonation of (R)-(+)-p-tolyl methyl sulfoxide and treatment of the resulting sulfinyl carbanion with phenyl chloroformate (eq 1).1

Asymmetric oxidation of phenyl (p-toluenesulfinyl)acetate with bovine serum albumin (BSA) gave a poor ee (eq 2).2

General Discussion.

Aldol-type condensation of the magnesium enolate of (R)-(+)-phenyl (p-toluenesulfinyl)acetate, prepared with t-butylmagnesium bromide, with the aldehyde precursor of maytansine afforded, after desulfurization with Aluminum Amalgam, the desired 4,5-unsaturated 3-(S)-hydroxy ester in high yield and high diastereoselectivity (eq 3).1

1. Corey, E. J.; Weigel, L. O.; Chamberlin, R.; Cho, H.; Hua, D. H. JACS 1980, 102, 6615.
2. Colonna, S.; Banfi, S.; Fontana, F.; Sommaruga, M. JOC 1985, 769.

Guy Solladié & Françoise Colobert

University Louis Pasteur, Strasbourg, France

Copyright 1995-2000 by John Wiley & Sons, Ltd. All rights reserved.