Current Organocatalysis

Bimal K. Banik
Vice President of Research & Education Development
Community Health Systems of South Texas (CHSST)
Edinburg, Texas
USA

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Low Catalyst Loading, Highly Efficient D-glucosamine-derived Organocatalysts for Asymmetric Aldol Reactions

Author(s): Hanxiao Liao, Chao Shen, Fangyi Shen, Pengfei Zhang, Weike Su.

Graphical Abstract:


Abstract:

Glucosamine as a kind of important nature chiral scaffold is widely regarded for its obvious advantages such as cheap, stable and readily available. In this communication, we reported the introduction of L-proline group at the amino functional group of D-glucosamine resulted in several efficient prolinamide organocatalysts, which could efficiently catalyze the asymmetric aldol reaction between acetone and various substituted benzaldehydes in the neat condition. Under the optimized conditions, 0.5 mol% of organocatalyst gave excellent chiral selectivity (83% ee value) with 88% yield, which was higher than that obtained using 10 mol% of organocatalyst.

Keywords: Aldol reaction, asymmetric catalysis, carbohydrate, organocatalyst.

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Article Details

VOLUME: 2
ISSUE: 1
Year: 2015
Page: [71 - 76]
Pages: 6
DOI: 10.2174/2213337202666141210214540