Acid-free, organocatalytic acetalization

Acid-free, organocatalytic acetalization
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DOI:
10.1016/j.tet.2005.09.079
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发表时间:
2006-01-09
期刊:
影响因子:
2.1
通讯作者:
Schreiner, PR
Schreiner, PR
中科院分区:
化学3区
文献类型:
--
作者:
Kotke, M;Schreiner, PR

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研究了N,N-双[3,5-二(三氟甲基)苯基]硫脲与醛、酮的无酸有机催化缩醛化反应。该中性双氢键硫脲催化剂可以在室温下以0.01-1摩尔%的非常低的负载量使用,以在约600小时(-1)的转换频率下以65-99%的产率提供相应的缩醛。酸不稳定的TBDMS保护的以及不饱和醛可以有效地转化为缩醛利用这种非常温和和高度实用的方法。(c)2005爱思唯尔有限公司保留所有权利。
The acid-free, organocatalytic acetalization of various aldehydes and ketones with NN-bis[3,5-bis(trifluoromethyl)phenyl] thiourea is presented. The neutral, double hydrogen bonding thiourea catalyst can be used at very low loadings of 0.01-1 mol% at room temperature to furnish the respective acetals in 65-99% yield at turnover frequencies around 600 h(-1). Acid-labile TBDMS-protected as well as unsaturated aldehydes can be converted efficiently into their acetals utilizing this very mild and highly practical method. (c) 2005 Elsevier Ltd. All rights reserved.