Organic letters

Hiyama cross-coupling reaction in the stereospecific synthesis of retinoids

J Montenegro, J Bergueiro, C Saá, S López

Index: Montenegro, Javier; Bergueiro, Julian; Saa, Carlos; Lopez, Susana Organic Letters, 2009 ,  vol. 11,  # 1  p. 141 - 144

Full Text: HTML

Citation Number: 22

Abstract

The first application of the Hiyama reaction to the synthesis of retinoids is reported. A range of organosilicon moieties (siloxanes, silanols and three kinds of “safety-catch” silanols) were successfully coupled, under activation, to obtain trans-retinol or 11-cis-retinol with high yield and stereoselectivity. The advantageous properties of the silicon-based coupling partners and the mild reaction conditions firmly establish the Hiyama reaction as a viable (even ...