Synthesis of azepines by a gold-catalyzed intermolecular [4 + 3]-annulation

Nathan D Shapiro; F Dean Toste

doi:10.1021/ja803890t

Synthesis of azepines by a gold-catalyzed intermolecular [4 + 3]-annulation

J Am Chem Soc. 2008 Jul 23;130(29):9244-5. doi: 10.1021/ja803890t. Epub 2008 Jun 25.

Authors

Nathan D Shapiro¹, F Dean Toste

Affiliation

¹ Department of Chemistry, University of California, Berkeley, California 94720, USA.

Abstract

A convenient gold(III)-catalyzed synthesis of azepines from the intermolecular annulation of propargyl esters and alpha,beta-unsaturated imines is reported (19 examples, 55-95% yield). This formal [4 + 3]-cycloaddition reaction is proposed to proceed via a stepwise process involving intramolecular trapping of an allyl-gold intermediate.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Allyl Compounds / chemistry
Azepines / chemical synthesis*
Catalysis
Cyclization
Gold / chemistry*
Organometallic Compounds / chemistry

Substances

Allyl Compounds
Azepines
Organometallic Compounds
Gold

Abstract

Publication types

MeSH terms

Substances

Grants and funding