Unprecedented rearrangement of a 4-alkoxy-5-bromoalk-2-en-1-ol to a cyclopentenone via an iso-nazarov cyclization process

Michael E Jung; Dongwon Yoo

doi:10.1021/jo071104w

Unprecedented rearrangement of a 4-alkoxy-5-bromoalk-2-en-1-ol to a cyclopentenone via an iso-nazarov cyclization process

J Org Chem. 2007 Oct 26;72(22):8565-8. doi: 10.1021/jo071104w. Epub 2007 Oct 2.

Authors

Michael E Jung¹, Dongwon Yoo

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90064-1569, USA. jung@chem.ucla.edu

PMID: 17910498
DOI: 10.1021/jo071104w

Abstract

We report the structure determination of the product 9 of the rearrangement of the allylic alcohol 3 under very mild conditions, probably promoted by an acidic substance, and propose a reasonable mechanism for its formation.

Publication types

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

MeSH terms

Alkenes / chemistry*
Cyclization
Cyclopentanes / chemical synthesis*
Cyclopentanes / chemistry
Molecular Conformation
Stereoisomerism

Substances

Alkenes
Cyclopentanes
cyclopentenone