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Highly stereoselective titanium-mediated aldol reactions from chiral α-silyloxy ketones. A reliable tool for the synthesis of natural products

Authors :
Carme Jimenez
Judit Esteve
Pedro Romea
Javier Velasco
Joaquim Nebot
Fèlix Urpí
Source :
Tetrahedron. 67:6045-6056
Publication Year :
2011
Publisher :
Elsevier BV, 2011.

Abstract

Chiral α-silyloxy ketones participate in highly stereoselective TiCl4-mediated aldol reactions that afford diastereomerically pure syn–syn adducts in high yield irrespective of the R1 and R2 substituents flanking the carbonyl or the silicon protecting group. Further manipulation of the resulting aldol adducts provide in a straightforward manner highly functionalized fragments that facilitate the synthesis of natural products.

Details

ISSN :
00404020
Volume :
67
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi...........c30290ef0a176a057a535a5dcf374aa3