Organocatalytic Enantioselective Oxidative C-H Alkenylation and Arylation of N-Carbamoyl Tetrahydropyridines and Tetrahydro-β-carbolines

Angew Chem Int Ed Engl. 2015 May 11;54(20):6012-5. doi: 10.1002/anie.201500703. Epub 2015 Mar 25.

Abstract

The first organocatalytic enantioselective C-H alkenylation and arylation reactions of N-carbamoyl tetrahydropyridines and tetrahydro-β-carbolines (THCs) are described. The metal-free processes represent an efficient and straightforward approach to a variety of structurally and electronically diverse α-substituted tetrahydropyridines and THCs in good yields with excellent regio- and enantioselectivities. Preliminary control experiments provide important insights into the reaction mechanism.

Keywords: CH functionalization; asymmetric organocatalysis; carbamates; tetrahydro-β-carbolines; tetrahydropyridines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Boronic Acids / chemistry*
  • Carbolines / chemistry*
  • Molecular Conformation
  • Oxidation-Reduction
  • Pyridines / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Boronic Acids
  • Carbolines
  • Pyridines