Highly Stereoselective Metal-Free Hydrogenations of Pyrrolo[1,2- a]quinoxalines

Xiaoqin Liu; Ting Liu; Wei Meng; Haifeng Du

doi:10.1021/acs.orglett.8b02364

Highly Stereoselective Metal-Free Hydrogenations of Pyrrolo[1,2- a]quinoxalines

Org Lett. 2018 Sep 21;20(18):5653-5656. doi: 10.1021/acs.orglett.8b02364. Epub 2018 Sep 4.

Authors

Xiaoqin Liu^{1

2}, Ting Liu^{1

2}, Wei Meng^{1

2}, Haifeng Du^{1

2}

Affiliations

¹ Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences , Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190 , China.
² School of Chemical Science , University of Chinese Academy of Sciences , Beijing 100049 , China.

PMID: 30179008
DOI: 10.1021/acs.orglett.8b02364

Abstract

A metal-free hydrogenation of pyrrolo[1,2- a]quinoxalines has been successfully realized by using the combination of B(C₆F₅)₃ and tris(4-methoxyphenyl)phosphine to furnish the corresponding 1,2,3,3a,4,5-hexahydropyrrolo[1,2- a]quinoxalines in 59-99% yields. For 4-aryl-substituted pyrrolo[1,2- a]quinoxalines, high cis selectivities were obtained, but trans-selectivities were achieved for the 4-methyl-substituted substrates.

Publication types

Research Support, Non-U.S. Gov't