文献类型：期刊文献

英文题名：Enantioselective [4+2] cycloaddition reaction of α,β-unsaturated imine and methyl vinyl ketone catalyzed by chiral phosphine

作者：Wang, Ge[1,2];Rexiti, Rukeya[1,2];Sha, Feng[1,2];Wu, Xin-Yan[1,2,3]

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

年份：2015

卷号：71

期号：24

起止页码：4255

外文期刊名：TETRAHEDRON

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000356114200022)】；

基金：We are grateful for the financial support from the National Natural Science Foundation of China (21242007, 21102043), Science and Technology Commission of Shanghai Municipality (15ZR1409200), and the Fundamental Research Funds for the Central Universities.

语种：英文

外文关键词：Asymmetric [4+2] cycloaddition; Bifunctional phosphines; Enantioselective organocatalysis; Tetrahydropyridine

摘要：New bifunctional phosphines were prepared as chiral organocatalysts for the enantioselective [4+2] cycloaddition between alpha,beta-unsaturated imines and methyl vinyl ketone. In the presence of 10 mol % of amide-phosphine, the [4+2] cycloaddition reaction was achieved in good-to-excellent yields (up to 95%) and diastereoselectivities (up to 99:1 dr) with moderate-to-good enantioselectivities (up to 82% ee). This methodology establishes a new protocol for the asymmetric construction of functionalized tetrahydropyridines. (C) 2015 Elsevier Ltd. All rights reserved.