期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 41, 页码 13089-13093出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404215
关键词
acetaldehyde; cross-aldol; recycling; site-isolation; wolf and lamb
资金
- Institute of Chemical Research of Catalonia (ICIQ) Foundation
- MINECO [CTQ2012-38594-C02-01, SEV-2013-0319]
- DEC Generalitat de Catalunya [2014SGR827]
- CSC (Chinese Scholarship Council)
- AGAUR (Generalitat de Catalunya)
Polystyrene-supported (PS) diarylprolinol catalysts 1a (Ar=phenyl) and 1b (Ar=3,5-bis(trifluoromethyl)phenyl) have been developed. Operating under site-isolation conditions, PS-1a/1b worked compatibly with PS-bound sulfonic acid catalyst 2 to promote deoligomerization of paraldehyde and subsequent cross-aldol reactions of the resulting acetaldehyde in one pot, affording aldol products in high yields with excellent enantioselectivities. The effect of water on the performance of the catalytic system has been studied and its optimal amount (0.5 equiv) has been determined. The dual catalytic system (1/2) allows repeated recycling and reuse (10 cycles). The potential of this methodology is demonstrated by a two-step synthesis of a phenoperidine analogue (68% overall yield; 98% ee) and by the preparation of highly enantioenriched 1,3-diols 4 and 3-methylamino-1-arylpropanols 5, key intermediates in the synthesis of a variety of druglike structures.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据