Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones

Megan H Shaw; Ekaterina Y Melikhova; Daniel P Kloer; William G Whittingham; John F Bower

doi:10.1021/ja401936c

Directing group enhanced carbonylative ring expansions of amino-substituted cyclopropanes: rhodium-catalyzed multicomponent synthesis of N-heterobicyclic enones

J Am Chem Soc. 2013 Apr 3;135(13):4992-5. doi: 10.1021/ja401936c. Epub 2013 Mar 22.

Authors

Megan H Shaw¹, Ekaterina Y Melikhova, Daniel P Kloer, William G Whittingham, John F Bower

Affiliation

¹ School of Chemistry, University of Bristol , Bristol BS8 1TS, United Kingdom.

PMID: 23488745
DOI: 10.1021/ja401936c

Abstract

Aminocyclopropanes equipped with suitable N-directing groups undergo efficient and regioselective Rh-catalyzed carbonylative C-C bond activation. Trapping of the resultant metallacycles with tethered alkynes provides an atom-economic entry to diverse N-heterobicyclic enones. These studies provide a blueprint for myriad N-heterocyclic methodologies.

Publication types

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

MeSH terms

Amines / chemistry*
Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Catalysis
Cyclopropanes / chemistry*
Ketones / chemistry*
Molecular Structure
Rhodium / chemistry*

Substances

Amines
Bridged Bicyclo Compounds, Heterocyclic
Cyclopropanes
Ketones
Rhodium