Novel Prolinamide Organocatalysts Based on Calix[4]arene Scaffold for the Enantioselective Direct Aldol Reaction

Zheng-Yi      Li; Cheng-Xi      Lu; Guoli      Huang; Jie-Jie      Ma; Hongsheng      Sun; Leyong      Wang; Yi      Pan

doi:10.2174/157017810791824919

Abstract

A series of novel prolinamide organocatalysts based on calix[4]arene scaffold have been developed to catalyze the direct asymmetric aldol reaction of aromatic aldehydes and cyclohexanone. Under the optimal condition, high isolated yields (up to > 99%) and enantioselectivities (up to 97% ee), and moderate diastereoselectivities (up to 85/15) were obtained.

Keywords: Prolinamide, calix[4]arene, organocatalyst, asymmetric aldol reaction

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Letters in Organic Chemistry

Title: Novel Prolinamide Organocatalysts Based on Calix[4]arene Scaffold for the Enantioselective Direct Aldol Reaction

Volume: 7 Issue: 6

Author(s): Zheng-Yi Li, Cheng-Xi Lu, Guoli Huang, Jie-Jie Ma, Hongsheng Sun, Leyong Wang and Yi Pan

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Keywords: Prolinamide, calix[4]arene, organocatalyst, asymmetric aldol reaction

Abstract: A series of novel prolinamide organocatalysts based on calix[4]arene scaffold have been developed to catalyze the direct asymmetric aldol reaction of aromatic aldehydes and cyclohexanone. Under the optimal condition, high isolated yields (up to > 99%) and enantioselectivities (up to 97% ee), and moderate diastereoselectivities (up to 85/15) were obtained.

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Li Zheng-Yi, Lu Cheng-Xi, Huang Guoli, Ma Jie-Jie, Sun Hongsheng, Wang Leyong and Pan Yi, Novel Prolinamide Organocatalysts Based on Calix[4]arene Scaffold for the Enantioselective Direct Aldol Reaction, Letters in Organic Chemistry 2010; 7 (6) . https://dx.doi.org/10.2174/157017810791824919