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Bifunctional Phosphine-Catalyzed Domino Reaction: Highly Stereoselective Synthesis of cis-2,3-Dihydrobenzofurans from Salicyl N-Thiophosphinyl Imines and Allenes

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posted on 01.01.2009, 00:00 by Xiangtai Meng, You Huang, Ruyu Chen
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.