Issue 96, 2014

Chemoselective silyl transfer in the Mukaiyama aldol reaction promoted by super silyl Lewis acid

Abstract

In the silyl Lewis acid-promoted Mukaiyama aldol reaction, the steric and electronic properties of the silyl group on the silyl Lewis acid influence the reaction mechanism and product distribution. When super silyl triflates such as (TMS)3SiOTf and (TES)3SiOTf are used as Lewis acids, the silyl group of the silyl enol ether chemoselectively transfers to the product. The mechanistic details have been investigated using density functional theory (DFT) calculations.

Graphical abstract: Chemoselective silyl transfer in the Mukaiyama aldol reaction promoted by super silyl Lewis acid

Supplementary files

Article information

Article type
Communication
Submitted
26 Jul 2014
Accepted
13 Oct 2014
First published
23 Oct 2014

Chem. Commun., 2014,50, 15206-15208

Chemoselective silyl transfer in the Mukaiyama aldol reaction promoted by super silyl Lewis acid

M. Sai, M. Akakura and H. Yamamoto, Chem. Commun., 2014, 50, 15206 DOI: 10.1039/C4CC05807K

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