Fluoride-assisted regioselective conversion of functionalized furans to alpha-substituted gamma-hydroxybutenolides using singlet oxygen

Santoshkumar N Patil; Fei Liu

doi:10.1021/jo070666c

Fluoride-assisted regioselective conversion of functionalized furans to alpha-substituted gamma-hydroxybutenolides using singlet oxygen

J Org Chem. 2007 Aug 3;72(16):6305-8. doi: 10.1021/jo070666c. Epub 2007 Jul 13.

Authors

Santoshkumar N Patil¹, Fei Liu

Affiliation

¹ Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, New South Wales 2109, Australia.

PMID: 17629339
DOI: 10.1021/jo070666c

Abstract

A facile synthesis of alpha-substituted gamma-hydroxybutenolides from 3-furfural was achieved using a Baylis-Hillman reaction followed by singlet oxygen oxidation. The regioselectivity of this conversion was controlled by using TBAF.

Publication types

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

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemistry
Catalysis
Chemistry, Organic / methods*
Fluorides / chemistry*
Furans / chemistry*
Models, Chemical
Oxygen / chemistry
Quaternary Ammonium Compounds / chemistry
Singlet Oxygen* / chemistry
Stereoisomerism

Substances

Furans
Quaternary Ammonium Compounds
Singlet Oxygen
butenolide
4-Butyrolactone
Fluorides
Oxygen