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Synthesis of Phosphoramides for the Lewis Base-Catalyzed Allylation and Aldol Addition Reactions

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journal contribution
posted on 03.03.1999, 00:00 by Scott E. Denmark, Xiping Su, Yutaka Nishigaichi, Diane M. Coe, Ken-Tsung Wong, Stephen B. D. Winter, Jun Young Choi
Both chiral and achiral phosphoramides of diverse structure were prepared from diamines by the coupling to phosphorus(V) or phosphorus(III) reagents. Several enantiopure 1,2-diphenyl-1,2-ethanediamine analogues have been prepared by the reductive coupling of the corresponding N-silylimine with NbCl4(THF)2 and subsequent resolution by the formation of diastereomeric menthyl carbamates. (S,S)-N,N‘-Di-(1-naphthyl)-1,2-diphenyl-1,2-ethanediamine 15 was prepared by the arylation of (S,S)-1,2-diphenyl-1,2-ethanediamine with naphthyl iodide.