Pd(OAc)2-catalyzed cyclization of 2,3-allenoic acids in the presence of terminal alpha,beta-unsaturated alkynones: a one-pot highly stereoselective synthesis of 4-(3'-oxo-1'(E)-alkenyl)-2(5H)-furanones

Guofei Chen; Rong Zeng; Zhenhua Gu; Chunling Fu; Shengming Ma

doi:10.1021/ol801610w

Pd(OAc)2-catalyzed cyclization of 2,3-allenoic acids in the presence of terminal alpha,beta-unsaturated alkynones: a one-pot highly stereoselective synthesis of 4-(3'-oxo-1'(E)-alkenyl)-2(5H)-furanones

Org Lett. 2008 Oct 2;10(19):4235-8. doi: 10.1021/ol801610w. Epub 2008 Aug 30.

Authors

Guofei Chen¹, Rong Zeng, Zhenhua Gu, Chunling Fu, Shengming Ma

Affiliation

¹ Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, P. R. China.

PMID: 18759431
DOI: 10.1021/ol801610w

Abstract

The Pd(OAc) 2-catalyzed cyclization reaction of 2,3-allenoic acids in the presence of terminal alpha,beta-unsaturated alkynones afforded an E/ Z mixture of 4-(3'-oxo-1'-alkenyl)-2(5 H)-furanones. A subsequent complete isomerization of the Z-isomer to E-isomer was observed in DMSO at 90 degrees C, which led to a highly stereoselective synthesis of 4-(3'-oxo-1'( E)-alkenyl)-2(5 H)-furanones. A possible mechanism is proposed.