Reactivity of gamma-hydroxy-alpha,beta-acetylenic esters with amines: facile synthesis of the optically active 4-amino-2(5H)-furanones

Li-Hong Zhou; Xiao-Qi Yu; Lin Pu

doi:10.1021/jo802592h

Reactivity of gamma-hydroxy-alpha,beta-acetylenic esters with amines: facile synthesis of the optically active 4-amino-2(5H)-furanones

J Org Chem. 2009 Mar 6;74(5):2013-7. doi: 10.1021/jo802592h.

Authors

Li-Hong Zhou¹, Xiao-Qi Yu, Lin Pu

Affiliation

¹ Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA.

PMID: 19195982
DOI: 10.1021/jo802592h

Abstract

A convenient synthesis of the optically active 4-amino-2(5H)-furanones is discovered by combining an asymmetric alkyne addition to aldehydes and a subsequent aliphatic amine addition. Both steps can be conducted at room temperature and the products are obtained with high enantioselectivity (84-90% ee). The 4-amino-2(5H)-furanones are also found to undergo very facile electrophilic substitution reactions.

Publication types

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

MeSH terms

Aldehydes / chemistry
Alkynes / chemistry
Amines / chemistry*
Esters
Furans / chemical synthesis*
Furans / chemistry
Molecular Conformation
Stereoisomerism

Substances

Aldehydes
Alkynes
Amines
Esters
Furans