Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (6): 1051-1056.doi: 10.1007/s40242-014-4212-x

• Articles • Previous Articles     Next Articles

Non-cross-linked Polystyrene Supported Cyclosulfamide: A New Chiral Auxiliary for Highly Stereoselective Alkylation Reactions

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

  1. Hubei Collaborative Innovation Center for Advanced Organochemical Materials, Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, Hubei University, Wuhan 430062, P. R. China
  • Received:2014-07-09 Revised:2014-08-08 Online:2014-12-01 Published:2014-08-13
  • Contact: LU Cuifen E-mail:lucf@hubu.edu.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.21342002) and the College Students' Innovation and Entrepreneurship Training Plan of Hubei Province of China(No.201310512013).

Abstract:

The asymmetric alkylation reactions induced by non-cross-linked polystyrene supported cyclosulfamide chiral auxiliary occurred in moderate to good yields with a very high stereoselectivity(e.e.>99%). Compared to non-supported cyclosulfamide chiral auxiliary, this chiral auxiliary can be recovered by simple precipitation and filtration, and could be reused at least four cycles without appreciable reduction in the yield or stereoselectivity.

Key words: Polystyrene, Cyclosulfamide, Chiral auxiliary, Alkylation reaction