V. Aggarwal, S. J. Masters, H. Adams
1999
Citations
0
Influential Citations
7
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
The reaction of tartrate-derived silylketene acetals and benzaldehyde has been investigated and the yields and diastereoselectivities have been found to be dependent upon the nature of the tartrate ester. Utilising the di-tert-butyl tartrate derivatives, high yields were achieved using a variety of aldehyde substrates. The reactions all proceeded with excellent levels of stereoselectivity ( 82∶18); the sense of induction being dependent upon the choice of Lewis acid. BF3·OEt2 and TiCl3(OiPr) furnished complementary products in several cases and a model has been proposed to account for this observation.