Polyvinylidene chloride supported L‐prolineamide as recoverable catalyst for asymmetric aldol reaction between ketone and aromatic aldehyde

羟醛反应 环己酮 化学 催化作用 溶剂 有机化学 有机催化 对映选择合成
作者
Xuan Zhang,Wei Zhao,Lili Yang,Yuanchen Cui
出处
期刊:Journal of Applied Polymer Science [Wiley]
卷期号:127 (5): 3537-3542 被引量:7
标识
DOI:10.1002/app.37645
摘要

Abstract A series of prolineamide modified by polyvinylidene chloride (PVDC) was synthesized and used as green recoverable organocatalysts for the asymmetric Aldol reactions between various ketones and aromatic aldehydes. The effects of solvent and catalyst dosage on the catalytic performances of as‐synthesized organocatalysts were investigated. It was found that as‐synthesized PVDC‐supported L ‐prolineamides possessed good catalytic performance for the asymmetric Aldol reactions between cyclohexanone and a variety of aromatic aldehydes, affording high yields of up to 99%, excellent diastereoselectivities of up to above 8 : 92 d.r. value, and high enantioselectivities of up to above 92.3% e.e. value. In general, the catalytic performance of as‐synthesized organocatalysts closely depended on the catalyst dosage and solvent type as well. Particularly, as‐synthesized organocatalyst 1c, at a dosage of 5 mol % in 10 μL of water, exhibited high catalytic activity and stereoselectivity for the asymmetric Aldol reaction between cyclohexanone and p ‐nitrobenzaldehyde at room temperature. In the meantime, it could be easily recovered and recycled, while the activity and enantioselectivity were nearly completely retained even after five cycles of recovery, showing promising application as an efficient green organocatalyst for the aforementioned asymmetric Aldol reactions. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013
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