Tetrahydroquinolines and benzazepines through catalytic diastereoselective formal [4 + 2]-cycloaddition reactions between donor-acceptor cyclopropenes and imines

Phong M Truong; Michael D Mandler; Peter Y Zavalij; Michael P Doyle

doi:10.1021/ol401308d

Tetrahydroquinolines and benzazepines through catalytic diastereoselective formal [4 + 2]-cycloaddition reactions between donor-acceptor cyclopropenes and imines

Org Lett. 2013 Jul 5;15(13):3278-81. doi: 10.1021/ol401308d. Epub 2013 Jun 18.

Authors

Phong M Truong¹, Michael D Mandler, Peter Y Zavalij, Michael P Doyle

Affiliation

¹ Department of Chemistry & Biochemistry, University of Maryland, College Park, Maryland 20742, USA.

PMID: 23777207
DOI: 10.1021/ol401308d

Abstract

Regio- and diastereoselective Lewis acid catalyzed cycloaddition reactions between imines and donor-acceptor cyclopropenes generated from silyl-protected enoldiazoacetates provide direct access to stable cyclopropane-fused tetrahydroquinolines and, with cyclopropane ring opening under mild conditions, to 1H-benzazipine derivatives.

Publication types

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

MeSH terms

Benzazepines / chemistry*
Catalysis
Cycloaddition Reaction
Cyclopropanes / chemistry*
Imines / chemistry*
Models, Molecular
Molecular Structure
Quinolines / chemical synthesis*
Quinolines / chemistry*
Stereoisomerism

Substances

Benzazepines
Cyclopropanes
Imines
Quinolines
cyclopropane
1,2,3,4-tetrahydroquinoline