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1. Stereoselective Synthesis of Diazabicyclic β-Lactams through Intramolecular Amination of Unactivated C(sp3)-H Bonds of Carboxamides by Palladium Catalysis.

Author

Shi-Jin Zhang, Wen-Wu Sun, Pei Cao, Xiao-Ping Dong, Ji-Kai Liu, and Bin Wu

Subjects
*LACTAMS, *CHEMICAL synthesis, *STEREOSELECTIVE reactions, *AMINATION, *CARBON-hydrogen bonds, *CARBOXAMIDES, *ACTIVATION (Chemistry), *PALLADIUM catalysts
Abstract

An efficient C(sp³)-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. [ABSTRACT FROM AUTHOR]

Published
2016
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