Synthesis of (Z)-vinylsilanes with high diastereoselectivity by using samarium diiodide

Authors
Concellon, JM Bernad, PL Bardales, E
Citation
Jm. Concellon et al., Synthesis of (Z)-vinylsilanes with high diastereoselectivity by using samarium diiodide, ORG LETT, 3(6), 2001, pp. 937-939
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
6
Year of publication
2001
Pages
937 - 939
Database
ISI
SICI code
1523-7060(20010322)3:6<937:SO(WHD>2.0.ZU;2-U
Abstract
[GRAPHICS] Beta-Elimination of O-acetyl 1-chloro-1-trimethylsilylalkan-2-ols 1 was ach ieved by using samarium diiodide as a metaling reagent and afforded the cor responding (Z)-vinylsilanes with high stereoselectivity. The starting compo unds 1 were easily prepared by treatment of different aldehydes with (chlor olithiomethyl)trimethylsilane and further acetylation.