Titanium chloride-mediated reactions of the silyl ketene acetals derived from N-methylephedrine esters: an asymmetric variant of the Mukaiyama reaction

C Gennari, L Colombo, G Bertolini…

Index: Gennari, Cesare; Colombo, Lino; Bertolini, Giorgio Journal of the American Chemical Society, 1986 , vol. 108, # 20 p. 6394 - 6395

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Citation Number: 59

Abstract

The TiC1,-mediated reaction between silyl ketene acetals 2 and benzaldehyde was chosen as a model for mechanistic studies. The influence of the silyl ketene acetal double-bond geometry, the C-1/C-2 relative configuration of N-methylephedrine, and different modes of addition and molar ratios of the reagents on the stereochemical outcome of the reaction was investigated. On the basis of these results and of literature data, an octahedral, six- ...