Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (3): 618-624.DOI: 10.6023/cjoc201412049 Previous Articles     Next Articles



徐靖坤, 谷永红, 田仕凯   

  1. 中国科学技术大学化学系 合肥 230026
  • 收稿日期:2014-12-29 修回日期:2015-01-17 发布日期:2015-01-20
  • 通讯作者: 谷永红, 田仕凯;
  • 基金资助:

    国家自然科学基金(Nos. 21472178和21232007)、国家重点基础研究发展计划(No. 2014CB931800)和安徽省自然科学基金(No. 1408085MB24)资助项目.

Enantiospecific Allylic Alkylation of Substituted Hydrazines with Allylic Alcohols

Xu Jing-Kun, Gu Yonghong, Tian Shi-Kai   

  1. Department of Chemistry, University of Science and Technology of China, Hefei 230026
  • Received:2014-12-29 Revised:2015-01-17 Published:2015-01-20
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21472178 and 21232007), the National Key Basic Research Program of China (No. 2014CB931800), and the Natural Science Foundation of Anhui Province of China (No. 1408085MB24).

Unprecedented enantiospecific allylic alkylation of substituted hydrazines with allylic alcohols has been developed. A range of substituted hydrazines underwent palladium/racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP)/boric acid-catalyzed allylic alkylation with highly enantioenriched allylic alcohols at room temperature and the reaction proceeded in a highly regioselective fashion with greater than 95% retention of configuration to afford allylic hydrazines with high enantiopurity. Moreover, only water was generated as an environmentally benign byproduct.

Key words: alcohols, hydrazines, allylic alkylation, palladium, enantiospecificity