有机催化杂[4+2]环加成反应 2-(1-炔基)-2-烯-1-酮：无金属条件下合成高取代的 4H-吡喃。

Organocatalytic hetero [4+2] cycloaddition reactions of 2-(1-alkynyl)-2-alkene-1-ones: metal-free access to highly substituted 4H-pyrans.

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N, Zhongshan Road, Shanghai 200062, PR China.

出版信息

Org Biomol Chem. 2010 Nov 21;8(22):5059-61. doi: 10.1039/c0ob00334d. Epub 2010 Sep 27.

DOI:10.1039/c0ob00334d

PMID:20871909

Abstract

Highly substituted 4H-pyrans can be smoothly synthesized from readily available 2-(1-alkynyl)-2-alkene-1-ones by DBU- or n-Bu(3)P catalyzed hetero-[4+2] cycloaddition reactions, in which 2-(1-alkynyl)-2-alkene-1-ones act as both heterodiene and heterodinenophile.

摘要

高度取代的 4H-吡喃可以通过 DBU 或 n-Bu(3)P 催化的杂 [4+2] 环加成反应，从易得的 2-(1-炔基)-2-烯烃-1-酮中顺利合成，其中 2-(1-炔基)-2-烯烃-1-酮既作为杂二烯又作为杂二烯亲核试剂。