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A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones with Aldedydes

Zhuo Tang, Zhi-Hua Yang, Xiao-Hua Chen, Lin-Feng Cun, Ai-Qiao Mi, Yao-Zhong Jiang and Liu-Zhu Gong*

*Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China, Email: gonglzcioc.ac.cn

Z. Tang, Z.-H. Yang, X.-H. Chen, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang, L.-Z. Gong, J. Am. Chem. Soc., 2005, 127, 9285-9289.

DOI: 10.1021/ja0510156 (free Supporting Information)


Abstract

L-Proline amides derived from various chiral β-amino alcohols were evaluated for catalyzing the direct Aldol reaction. A catalyst with strong electron-withdrawing groups was found to exhibit high catalytic activity and enantioselectivity for the aldol reaction of a wide range of aldehydes with acetone and butanone, to give β-hydroxy ketones.

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Key Words

Aldol Addition, β-Hydroxy Ketones, Organocatalysis


ID: J48-Y2005-2430