在末端α,β-不饱和炔酮存在下，醋酸钯催化2,3-联烯酸的环化反应：4-(3'-氧代-1'(E)-烯基)-2(5H)-呋喃酮的一锅法高立体选择性合成

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.

作者信息

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

机构信息

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

出版信息

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

DOI:10.1021/ol801610w

PMID:18759431

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.

摘要

在末端α,β-不饱和炔酮存在下，醋酸钯催化2,3-联烯酸的环化反应得到了4-(3'-氧代-1'-烯基)-2(5H)-呋喃酮的E/Z混合物。随后在90℃的二甲基亚砜中观察到Z-异构体完全异构化为E-异构体，这导致了4-(3'-氧代-1'(E)-烯基)-2(5H)-呋喃酮的高度立体选择性合成。提出了一种可能的机理。