催化学报 ›› 2015, Vol. 36 ›› Issue (1): 106-112.DOI: 10.1016/S1872-2067(14)60246-1

• 论文 • 上一篇    下一篇

Metal and organo-catalysed asymmetric hydroaminomethylation of styrenes

Barbara Villa-Marcos, Jianliang Xiao   

  1. Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
  • 收稿日期:2014-09-12 修回日期:2014-10-25 出版日期:2014-12-31 发布日期:2014-12-31
  • 通讯作者: Jianliang Xiao

Metal and organo-catalysed asymmetric hydroaminomethylation of styrenes

Barbara Villa-Marcos, Jianliang Xiao   

  1. Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
  • Received:2014-09-12 Revised:2014-10-25 Online:2014-12-31 Published:2014-12-31

摘要:

A new protocol that enables asymmetric hydroaminomethylation of styrenes to afford chiral amines has been developed. Catalysed by an Rh-phosphine species and a chiral phosphoric acid, styrenes are converted into β-chiral amines with good enantioselectivities under syngas in the presence of an amine and Hantzsch ester. The reaction involves two key steps, hydroformylation and reductive amination, with the former catalysed by the Rh species whilst the latter by the phosphoric acid.

关键词: Asymmetric hydroaminomethylation, Hydroformylation, Chiral amine, Metal catalysis, Organocatalysis

Abstract:

A new protocol that enables asymmetric hydroaminomethylation of styrenes to afford chiral amines has been developed. Catalysed by an Rh-phosphine species and a chiral phosphoric acid, styrenes are converted into β-chiral amines with good enantioselectivities under syngas in the presence of an amine and Hantzsch ester. The reaction involves two key steps, hydroformylation and reductive amination, with the former catalysed by the Rh species whilst the latter by the phosphoric acid.

Key words: Asymmetric hydroaminomethylation, Hydroformylation, Chiral amine, Metal catalysis, Organocatalysis