A copper(II)-mediated regioselective cyclization-acetoxylation of 6,8-dien-1-ones for the synthesis of functionalized cyclopentanes

Yazhou Wang; Haifeng Du

doi:10.1021/jo100413p

A copper(II)-mediated regioselective cyclization-acetoxylation of 6,8-dien-1-ones for the synthesis of functionalized cyclopentanes

J Org Chem. 2010 May 21;75(10):3503-6. doi: 10.1021/jo100413p.

Authors

Yazhou Wang¹, Haifeng Du

Affiliation

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

PMID: 20361750
DOI: 10.1021/jo100413p

Abstract

This paper describes a copper(II) acetate-mediated cyclization-acetoxylation of 6,8-dien-1-ones in the presence of sodium acetate as base. A variety of functionalized cyclopentanes containing synthetic useful allylic alcohol moieties with three contiguous stereogenic centers were synthesized in moderate to good yields with moderate to high regioselectivities.

Publication types

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

MeSH terms

Alkadienes / chemistry*
Copper / chemistry*
Cyclization
Cyclopentanes / chemical synthesis*
Cyclopentanes / chemistry
Molecular Structure
Organometallic Compounds / chemistry*
Stereoisomerism

Substances

Alkadienes
Cyclopentanes
Organometallic Compounds
Copper