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Synfacts 2006(5): 0504-0504
DOI: 10.1055/s-2006-934451
DOI: 10.1055/s-2006-934451
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Direct Aldol Reaction Based on Molecular Recognition
Z. Tang, L.-F. Cun, X. Cui, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong*
Chengdu Institute of Organic Chemistry and Graduate School of the Chinese Academy of Sciences, Beijing, P. R. of China
Further Information
Publication History
Publication Date:
21 April 2006 (online)
Significance
An organocatalytic asymmetric aldol reaction based on molecular recognition has been developed. Direct addition of ketones 1 to α-keto acids 2 in the presence of 20 mol% of chiral prolinamide 3 followed by subsequent esterification with diazomethane provides β-hydroxy ketones 4 in good yields and enantioselectivities. Both aromatic and aliphatic precursors 2 can be used. Additionally, a transition state to explain the observed absolute configuration is proposed.