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Synfacts 2006(3): 0242-0242
DOI: 10.1055/s-2006-931954
DOI: 10.1055/s-2006-931954
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Diastereoselective Synthesis of Vinylaziridenes
J.-C. Zheng, W.-W. Liao, X.-X. Sun, X.-L. Sun, Y. Tang, L.-X. Dai, J.-G. Deng*
Shanghai Institute of Organic chemistry and Chengdu Institute of Organic Chemistry, P. R. of China
Further Information
Publication History
Publication Date:
21 February 2006 (online)
Significance
A highly stereoselective synthesis of vinylaziridines is reported using telluronium allylide and enantiopure N- tert-butylsulfinimines. High cis selectivity (up to 30:1) and excellent diastereoselectivity (up to 98% de) were observed. LiHMDS was the optimal base in terms of yield and stereoselectivity. The counterion of the telluronium salt and additives influenced the yield and stereoselectivity of the reaction.