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Allylation reactions of acylsilanes as synthetic equivalents of aldehydes. Application to a stereocontrolled synthesis of (1S,2S,5S)-(10S)-and-(10R)-allyl myrtanol

✍ Scribed by Bianca Flavia Bonini; Mauro Comes-Franchini; Mariafrancesca Fochi; Germana Mazzanti; Cristiano Nanni; Alfredo Ricci

Book ID: 104259787
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 230 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)01413-0

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✦ Synopsis

The allylation of acylsilanes with tetraallyltin in the presence of catalytic amounts of Sc(OTI) 3 proceeded smoothly to afford the silylated homoallylic alcohols in good yields. Subsequent protiodesilylation gave the formal adducts of the corresponding aldehydes. The homochiral acylsilane II gave a reversal of as) mmetric induction in the Sc(OTf) 3 catalyzed allylation and in the Sakurai reaction.

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