Stereoselective Synthesis of Diazabicyclic β-Lactams through Intramolecular Amination of Unactivated C(sp(3))-H Bonds of Carboxamides by Palladium Catalysis

J Org Chem. 2016 Feb 5;81(3):956-68. doi: 10.1021/acs.joc.5b02532. Epub 2016 Jan 26.

Abstract

An efficient C(sp(3))-H bond activation and intramolecular amination reaction via palladium catalysis at the β-position of carboxyamides to make β-lactams was described. The investigation of the substrate scope showed that the current reaction conditions favored activation of the β-methylene group. Short sequences were developed for preparation of various diazabicyclic β-lactam compounds with this method as the key step from chiral proline and piperidine derivatives.

Publication types

  • Research Support, Non-U.S. Gov't