Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (2): 219-225.doi: 10.1007/s40242-016-5273-9

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Scope and Limitations of Optical Pure Hydantoins as Chiral Auxiliaries in Asymmetric Mannich Reactions

CHEN Feng, LU Cuifen, NIE Junqi, CHEN Zuxing, YANG Guichun   

  1. Hubei Collaborative Innovation Center for Advanced Organochemical Materials & Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062, P. R. China
  • Received:2015-07-17 Revised:2015-11-06 Online:2016-04-01 Published:2015-12-14
  • Contact: YANG Guichun E-mail:yangguichun@hubu.edu.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.21342002).

Abstract:

The Mannich reaction of various 5-substituted and N-acyl substituted chiral hydantoins with a series of aldimines smoothly occurred with full stereochemical control. These Mannich adducts have been cleaved by alcoholysis to afford several synthetically useful chiral building blocks like β-amino esters and β-lactams in good yields and in enantiopure form.

Key words: Scope, Limitation, Hydantoin, Chiral auxiliary, Mannich reaction