Enantioselective synthesis of aza-beta-lactams via NHC-catalyzed [2 + 2] cycloaddition of ketenes with diazenedicarboxylates

Xue-Liang Huang; Xiang-Yu Chen; Song Ye

doi:10.1021/jo901656q

Enantioselective synthesis of aza-beta-lactams via NHC-catalyzed [2 + 2] cycloaddition of ketenes with diazenedicarboxylates

J Org Chem. 2009 Oct 2;74(19):7585-7. doi: 10.1021/jo901656q.

Authors

Xue-Liang Huang¹, Xiang-Yu Chen, Song Ye

Affiliation

¹ Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

PMID: 19722509
DOI: 10.1021/jo901656q

Abstract

N-Heterocyclic carbenes were found to be efficient catalysts for the formal [2 + 2] cycloaddition of aryl(alkyl)ketenes and diazenedicarboxylates to give the corresponding aza-beta-lactams in good yields with up to 91% ee. The N-substituent (carboxylate vs benzoyl) of diazenes played an important role to control the reaction modes (formal [2 + 2] vs [4 + 2] cycloaddtions).

Publication types

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

MeSH terms

Catalysis
Cyclization
Dicarboxylic Acids / chemistry*
Ethylenes / chemistry*
Heterocyclic Compounds / chemistry*
Ketones / chemistry*
Methane / analogs & derivatives*
Methane / chemistry
Molecular Structure
Stereoisomerism
beta-Lactams / chemical synthesis*
beta-Lactams / chemistry

Substances

Dicarboxylic Acids
Ethylenes
Heterocyclic Compounds
Ketones
beta-Lactams
carbene
ketene
Methane