Enantioselective aza-Henry reaction using cinchona organocatalysts
Enantioselective aza-Henry reaction using cinchona organocatalysts
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DOI：
10.1016/j.tet.2005.09.076
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发表时间：
2006-01-09
期刊：
影响因子：
2.1
通讯作者：
Sgarzani, V
中科院分区：
文献类型：
--
作者：
Bernardi, L;Fini, F;Sgarzani, V
金鸡纳生物碱和改性金鸡纳碱促进了亚胺与硝基甲烷的氮杂-Henry反应，得到了光学活性的β-硝基胺。各种N-保护的亚胺作为底物进行了检查。N-Boc、N-Cbz和N-Fmoc保护的亚胺在化学产率和对映选择性方面给出了最好的结果。通过对一系列手性碱的筛选，在优化的反应条件下，以金鸡纳为基础的硫脲类有机催化剂对映体的选择性高达94%ee。(c)2005爱思唯尔有限公司保留所有权利。
The aza-Henry reaction of imines with nitromethane was promoted by cinchona alkaloids and modified cinchona bases to give optically active beta-nitroamines. Various N-protected imines were examined as substrates. N-Boc, N-Cbz, and N-Fmoc protected imines gave the best results in terms of chemical yields and enantioselectivities. After a careful screening of a series of chiral bases, very good enantioselectivities up to 94% ee were obtained using a cinchona-based thiourea organocatalyst under the optimized reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.