Asymmetric synthesis of cyclic beta-hydroxyallylsilanes via sequential allyltitanation-ring closing metathesis
(2004) Tetrahedron — Vol. 60, n° 34, p. 7325-7344 (2004)
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- Abstract
- Highly enantioenriched cyclic beta-hydroxyallyisilanes 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 beta-hydroxyallyisilanes reacted stereoselectively with a variety of electrophilic reagents. A first application of this method to the synthesis of a highly functionalized dihydropyrane is reported. (C) 2004 Elsevier Ltd. All rights reserved.
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Adam, J.-M., de Fays, L., Laguerre, M., & Ghosez, L. (2004). Asymmetric synthesis of cyclic beta-hydroxyallylsilanes via sequential allyltitanation-ring closing metathesis. Tetrahedron, 60(34), 7325-7344. https://doi.org/10.1016/j.tet.2004.05.058 (Original work published 2004)