Base-assisted regio- and diastereoselective conversion of functionalized furans to butenolides using singlet oxygen

Santoshkumar N Patil; Fei Liu

doi:10.1021/ol062551l

Base-assisted regio- and diastereoselective conversion of functionalized furans to butenolides using singlet oxygen

Org Lett. 2007 Jan 18;9(2):195-8. doi: 10.1021/ol062551l.

Authors

Santoshkumar N Patil¹, Fei Liu

Affiliation

¹ Department of Chemistry & Biomolecular Sciences, Macquarie University, Sydney, NSW 2109, Australia.

PMID: 17217263
DOI: 10.1021/ol062551l

Abstract

A facile synthesis of beta-functionalized gamma-hydroxybutenolides was achieved using a Baylis-Hillman reaction followed by singlet oxygen oxidation. The conversion from 3-furfural was regio- and diastereoselective. [reaction: see text].

Publication types

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

MeSH terms

4-Butyrolactone / analogs & derivatives
4-Butyrolactone / chemical synthesis*
4-Butyrolactone / chemistry
Furans / chemistry*
Molecular Structure
Oxygen / chemistry*
Stereoisomerism

Substances

Furans
4-Butyrolactone
Oxygen