Bifunctional Phosphine-Catalyzed Domino Reaction: Highly Stereoselective Synthesis of cis-2,3-Dihydrobenzofurans from Salicyl N-Thiophosphinyl Imines and Allenes
Bifunctional Phosphine-Catalyzed Domino Reaction: Highly Stereoselective Synthesis of cis-2,3-Dihydrobenzofurans from Salicyl N-Thiophosphinyl Imines and Allenes
复制标题
双功能膦催化的多米诺反应：从水杨基 N-硫代次膦基亚胺和丙二烯高度立体选择性合成顺式-2,3-二氢苯并呋喃
DOI：
10.1021/ol802453c
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发表时间：
2009-01-01
期刊：
影响因子：
5.2
通讯作者：
Chen, Ruyu
中科院分区：
文献类型：
--
作者：
Meng, Xiangtai;Huang, You;Chen, Ruyu
以水杨基N-硫代膦酰亚胺和缺电子联烯为原料，通过氮杂-Morita-Baylis-Hillman/umpolung加成多米诺反应合成了顺式-2，3-二氢苯并呋喃。双功能催化剂的亲核试剂和亲电试剂的双重活化解释了所观察到的高反应性和立体选择性。
A new bifunctional phosphine catalyst, (2'-hydroxy-biphenyl-2-yl)-diethylphosphane (LBBA-1), was developed for the highly stereoselective synthesis of cis-2,3-dihydrobenzofurans via an aza-Morita-Baylis-Hillman/umpolung addition domino reaction of salicyl N-thiophosphinyl Imines with electron-deficient allenes. Dual activation of both nucleophile and electrophile by the bifunctional catalyst accounts for the observed high reactivity and stereoselectivity.