A facile synthesis of enantiopure 2-aziridinesulfinimines and their highly diastereoselective reactions with phosphite anions.
Two novel enantiopure 1-benzyl-2-aziridinesulfinimines bearing a chiral group on both sides of the carbon-nitrogen double bond were synthesized from the condensation of racemic 1-benzyl-2-aziridinecarboxaldehyde and enantiopure p-toluenesulfinamide. The addition reaction with phosphite anion followed by the ring-opening reaction with thiophenol provided chiral alpha,beta-diamino-phosphonic acid derivatives. The addition reactions showed the operation of a double-stereodifferentiation effect. The possible transition states of the reaction were proposed, and high diastereoselectivities of the addition reactions of phosphite anions to both aziridinesulfinimines were realized in the presence or absence of zinc bromide.
Li
Bin-Feng
BF
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Zhang
Ming-Jie
MJ
Hou
Xue-Long
XL
Dai
Li-Xin
LX