(R)-(+)-a-(p-Tolylsulfinyl)-N,N-dimethylacetamide

[72298-22-7]  · C11H15NO2S  · (R)-(+)-a-(p-Tolylsulfinyl)-N,N-dimethylacetamide  · (MW 225.34)

(asymmetric aldol-type condensation1,2)

Physical Data: [a]D = +194.7° (CHCl3, c = 1).

Preparative Method: prepared1,2 by reaction of Lithio-N,N-dimethylacetamide with (S)-(-)-menthyl p-toluenesulfinate (see (-)-(1R,2S,5R)-Menthyl (S)-p-Toluenesulfinate) (eq 1).

The Pummerer reaction of optically active (R)-(+)-a-(p-tolylsulfinyl)-N,N-dimethylacetamide with Acetic Anhydride in the presence of 1,3-Dicyclohexylcarbodiimide is highly stereoselective, affording the corresponding a-acetoxy sulfide in moderate yield but with nearly 70% ee (eq 2).3,4 The recovered starting sulfoxide is obtained in 63% yield.

Good asymmetric induction is also observed during the aldol-type condensation of the magnesium enolate of (R)-(+)-a-(p-tolylsulfinyl)-N,N-dimethylacetamide with aldehydes (eq 3).1,2

A model (1), similar to that proposed for aldol-type condensation of a-sulfinyl esters,5 has been proposed to predict the chirality of the resulting b-hydroxy amides.


1. Annunziata, R.; Cinquini, M.; Cozzi, F.; Montanari, F.; Restelli, A. CC 1983, 1138.
2. Annunziata, R.; Cinquini, M.; Cozzi, F.; Montanari, F.; Restelli, A. T 1984, 40, 3815.
3. Numata, T.; Itoh, O.; Oae, S. TL 1979, 21, 1869.
4. Numata, T.; Itoh, O.; Yoshimura, T.; Oae, S. BCJ 1983, 56, 257.
5. Mioskowski, C.; Solladié, G. T 1980, 36, 227.

Guy Solladié & Françoise Colobert

University Louis Pasteur, Strasbourg, France



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