A highly asymmetric direct aldol reaction catalyzed by chiral proline amide – thiourea bifunctional catalysts

A highly asymmetric direct aldol reaction catalyzed by chiral proline amide – thiourea bifunctional catalysts

A series of chiral proline amide – thiourea bifunctional catalysts derived from l -proline and chiral diamine were prepared and successfully applied to highly enantioselective direct aldol reactions of cyclohexanone with various aldehydes in excellent yields (85%–97%), diastereoselectivities (anti/s...

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Veröffentlicht in:Canadian journal of chemistry 2011-11, Vol.89 (10), p.1312-1318
Hauptverfasser: Li, Yun, Yang, Qing-chuan, Xu, Xiao-Ying, Zhou, Yong, Bai, Jian-fei, Wang, Fei- ying, Wang, Li-xin
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
aldol reaction
amide–thiourea
amide–thiourée
bifunctional catalyst
catalyseur bifonctionnel
Catalysts
Chemical reactions
Cyclohexanone
Diamines
Enantiomers
Organosulfur compounds
Proline
réaction aldolique
Thioureas
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Zusammenfassung:A series of chiral proline amide – thiourea bifunctional catalysts derived from l -proline and chiral diamine were prepared and successfully applied to highly enantioselective direct aldol reactions of cyclohexanone with various aldehydes in excellent yields (85%–97%), diastereoselectivities (anti/syn > 20:1) and enantioselectivities (up to 91% ee).
ISSN:0008-4042
1480-3291
DOI:10.1139/v11-029