Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 65-70.DOI: 10.6023/cjoc202006013 Previous Articles     Next Articles



张怀远a,b,*(), Thomas Wirthb,*()   

  1. a 兰州石化职业技术学院 应用化学工程学院 兰州 730060
    b 卡迪夫大学化学学院 卡迪夫 CF10 3AT
  • 收稿日期:2020-06-09 修回日期:2020-07-09 发布日期:2020-08-11
  • 通讯作者: 张怀远, Thomas Wirth
  • 作者简介:
    * Corresponding authors. E-mail: ;
  • 基金资助:
    国家留学基金(201908620006); 甘肃省高等学校科学研究(2018B-091); 兰州石化职业技术学院教科研(JY2018-25)

Recent Advances in Asymmetric Functionalization of Olefins Induced by Chiral Hypervalent Iodine Reagents

Huaiyuan Zhanga,b,*(), Thomas Wirthb,*()   

  1. a School of Applied Chemical Engineering, Lanzhou Petrochemical Polytechnic, Lanzhou 730060
    b School of Chemistry, Cardiff University, Cardiff, CF10 3AT
  • Received:2020-06-09 Revised:2020-07-09 Published:2020-08-11
  • Contact: Huaiyuan Zhang, Thomas Wirth
  • Supported by:
    the China Scholarship Council(201908620006); the Scientific Research Projects of Colleges and Universities in Gansu Province(2018B-091); the Teaching and Scientific Research Project of Lanzhou Petrochemical Polytechnic(JY2018-25)

The functionalization of olefins induced by chiral hypervalent iodine reagents is a basic method for obtaining enantiomerically enriched chiral molecules and biologically active natural products. It is one of the new and promising fields in asymmetric synthesis. Throughout the past 20 years development in this area, on the one hand, stereoselective functionalizations of alkenes such as disulfonyloxylation, diacetoxylation, dihalogenation, diamination, hydroxylation-sulfonyloxylation and halogenation-alkylation and carbonylation have been successfully achieved with chiral hypervalent iodine reagents through intermolecular reactions, in which various functionalized products were enantioselectively obtained. On the other hand, many of hetero-cyclic compounds such as γ-butyrolactones, chromans, isochromans, oxazolidinones, piperidines, pyrrolidines and aziridines can be synthesized by intramolecular oxidative lactonization, etherification, amidation, arylation and other reactions, in which hypervalent iodine reagents can provide efficient methods for the synthesis of chiral heterocyclic compounds. In addition, various functionalization reactions of olefins mediated by chiral hypervalent iodine reagents can afford target compounds with excellent yield and enantioselectivity. Thus, this methodology has also been used in the total synthesis of natural products. The functionalization of olefins induced by chiral hypervalent iodine reagents and their applications in the total synthesis of natural products are reviewed.

Key words: Keywords chiral hypervalent iodine reagents, olefins, functionalization, asymmetric synthesis