Enantioselective aza-Diels-Alder reaction of Brassard's diene with aldimines catalyzed by chiral N,N′-dioxide-Yb(OTf)3 complex
Enantioselective aza-Diels-Alder reaction of Brassard's diene with aldimines catalyzed by chiral N,N′-dioxide-Yb(OTf)3 complex
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DOI：
10.1016/j.tetlet.2010.04.009
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发表时间：
2010-06-09
影响因子：
1.8
通讯作者：
Feng, Xiaoming
中科院分区：
文献类型：
--
作者：
Chen, Zhenling;Lin, Lili;Feng, Xiaoming
本文报道了手性N，N '-二氧-Yb（OTf）（3）络合物催化的双烯与醛亚胺的aza-Diels-桤木反应，在温和条件下，以中等产率和良好的对映选择性（高达81%ee，一次重结晶高达99%ee）得到相应的α，β-不饱和δ-内酰胺衍生物。反应中间体的分离表明该不对称氮杂-Diels-桤木反应通过逐步Mannich型途径进行。(C)2010爱思唯尔有限公司保留所有权利。
The chiral N,N'-dioxide-Yb(OTf)(3) complex-catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with aldimines has been developed, giving the corresponding alpha,beta-unsaturated delta-lactam derivatives in moderate yields with good enantioselectivities (up to 81% ee and up to 99% ee by single recrystallization) under mild conditions. Isolation of the reaction intermediate indicates that this asymmetric aza-Diels-Alder reaction proceeds through a stepwise Mannich-type pathway. (C) 2010 Elsevier Ltd. All rights reserved.