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Cu-catalyzed asymmetric conjugate additions of dialkyl- and diarylzinc reagents to acyclic beta-silyl-alpha,beta-unsaturated ketones. Synthesis of allylsilanes in high diastereo- and enantiomeric purity.

Authors :
Kacprzynski MA
Kazane SA
May TL
Hoveyda AH
Source :
Organic letters [Org Lett] 2007 Aug 02; Vol. 9 (16), pp. 3187-90. Date of Electronic Publication: 2007 Jun 30.
Publication Year :
2007

Abstract

A readily available and simple (MW = 444.5 g/mol) valine-based chiral phosphine is used to promote highly efficient catalytic asymmetric conjugate additions of dialkyl- and diarylzinc reagents to acyclic beta-silyl-alpha,beta-unsaturated ketones. The catalytic asymmetric protocol allows access to versatile allylsilanes that bear a trisubstituted olefin in high diastereo- and enantiomeric purity.

Details

Language :
English
ISSN :
1523-7060
Volume :
9
Issue :
16
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
17602643
Full Text :
https://doi.org/10.1021/ol071331k