Organocatalytic asymmetric C-H vinylation and arylation of N-acyl tetrahydroisoquinolines

Xigong Liu; Shutao Sun; Zhilin Meng; Hongxiang Lou; Lei Liu

doi:10.1021/acs.orglett.5b00909

Organocatalytic asymmetric C-H vinylation and arylation of N-acyl tetrahydroisoquinolines

Org Lett. 2015 May 15;17(10):2396-9. doi: 10.1021/acs.orglett.5b00909. Epub 2015 May 5.

Authors

Xigong Liu¹, Shutao Sun¹, Zhilin Meng¹, Hongxiang Lou¹, Lei Liu¹

Affiliation

¹ Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China.

PMID: 25941891
DOI: 10.1021/acs.orglett.5b00909

Abstract

The first organocatalytic enantioselective oxidative C-H functionalization of N-acyl tetrahydroisoquinolines with vinyl and aryl boronates promoted by a chiral Brønsted acid is described. This metal-free process tolerates a wide range of electronically varied N-acyl tetrahydroisoquinolines and structurally diverse boronates with good to excellent enantioselectivities.

Publication types

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

MeSH terms

Boronic Acids / chemistry*
Catalysis
Ethylene Chlorohydrin / analogs & derivatives*
Ethylene Chlorohydrin / chemistry
Molecular Structure
Stereoisomerism
Tetrahydroisoquinolines / chemistry*
Trifluoroethanol / chemistry*

Substances

Boronic Acids
Tetrahydroisoquinolines
Trifluoroethanol
Ethylene Chlorohydrin
2,2,2-trichloroethanol