Asymmetric synthesis of cyclic β-hydroxyallylsilanes via sequential allyltitanation-ring closing metathesis

JM Adam, L de Fays, M Laguerre, L Ghosez

Index: Adam, Jean-Michel; De Fays, Laurence; Laguerre, Michel; Ghosez, Leon Tetrahedron, 2004 , vol. 60, # 34 p. 7325 - 7344

Full Text: HTML

Citation Number: 23

Abstract

Highly enantioenriched cyclic β-hydroxyallylsilanes have been prepared via enantioselective allylation of unsaturated aldehydes using a chiral allyltitanium reagent, followed by a ring-closing metathesis. Functionalized rings of various sizes have been synthesized and the electronic effect of the silicon group in the RCM reaction has been studied. The resulting cyclic β-hydroxyallylsilanes reacted stereoselectively with a variety ...