ALLYLATION REACTIONS OF ACYLSILANES AS SYNTHETIC EQUIVALENTS OF ALDEHYDES, APPLICATION TO A STEREOCONTROLLED SYNTHESIS OF (1S,2S,5S)-(10S)-AND-(10R)-ALLYL MYRTANOL

Authors
BONINI BF COMESFRANCHINI M FOCHI M MAZZANTI G NANNI C RICCI A
Citation
Bf. Bonini et al., ALLYLATION REACTIONS OF ACYLSILANES AS SYNTHETIC EQUIVALENTS OF ALDEHYDES, APPLICATION TO A STEREOCONTROLLED SYNTHESIS OF (1S,2S,5S)-(10S)-AND-(10R)-ALLYL MYRTANOL, Tetrahedron letters, 39(37), 1998, pp. 6737-6740
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
37
Year of publication
1998
Pages
6737 - 6740
Database
ISI
SICI code
0040-4039(1998)39:37<6737:AROAAS>2.0.ZU;2-G
Abstract
The allylation of acylsilanes with tetraallyltin in the presence of ca talytic amounts of Sc(OTf)(3) proceeded smoothly to afford the silylat ed homoallylic alcohols in good yields. Subsequent protiodesilylation gave the formal adducts of the corresponding aldehydes. The homochiral acylsilane 1l gave a reversal of asymmetric induction in the Sc(OTf)( 3) catalyzed allylation and in the Sakurai reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.