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HERO ID
8450913
Reference Type
Journal Article
Title
Asymmetric, regioselective direct aldol coupling of enones and aldehydes with chiral rhodium(bis-oxazolinylphenyl) catalysts
Author(s)
Mizuno, M; Inoue, H; Naito, T; Zhou, L; Nishiyama, H
Year
2009
Is Peer Reviewed?
Yes
Journal
Chemistry: A European Journal
ISSN:
0947-6539
EISSN:
1521-3765
Volume
15
Issue
36
Page Numbers
8985-8988
Language
English
DOI
10.1002/chem.200901329
Abstract
A study was conducted to demonstrate asymmetric and regioselective direct aldol coupling of enones and aldehydes with chiral rhodium(bis-oxazolinphenyl) catalysts. It was demonstrated that the [Rh(Phebox) complex acted as a Lewis acid and a Brønsted base to to form a rhodium-enolate species. The rhodium complex 1a, compound 3, and silver trifluoromethanesulfonate were placed in a flask to conduct the investigations. The reaction mixture was directly introduced onto a silica-gel column and eluted with ethyl acetate and hexane to give the desired acetate product as a pale yellow. The diastereomeric ratio was determined by 1H NMR spectroscopy.
Keywords
Aldol reaction; Asymmetric catalysis; Dienolates; Enones; Rhodium
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