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Practical synthesis of (E)- and (Z)-2-silyl-3-penten-1-ols with high enantiopurity

✍ Scribed by Koichiro Fukuda; Masaaki Miyashita; Keiji Tanino

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 585 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.06.104

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✦ Synopsis

Practical methods for the synthesis of the optically active (E)-and (Z)-2-silyl-3-pentene-1-ols are described. The optically pure (E)-allylsilane was synthesized from commercially available (R)-3-butyn-2-ol in five steps involving hydrozirconation followed by alkylation of the resulting alkenylmetal with BnOCH 2 Cl. On the other hand, both enantiomers of the corresponding (Z)-allylsilane were prepared from commercially available dimethylphenylvinylsilane through epoxidation, the regioselective epoxideopening reaction with 1-propynylmagnesium bromide, and the subsequent optical resolution using a lipase.

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