通过串联共轭炔基化/Ag(I)催化内酯化，从 5-(1-芳基亚烷基)Meldrum's 酸中快速合成复杂的γ-丁内酯。

Expedient synthesis of complex γ-butyrolactones from 5-(1-arylalkylidene) meldrum's acids via sequential conjugate alkynylation/Ag(I)-catalyzed lactonization.

机构信息

Department of Chemistry, University of Waterloo , Waterloo, Ontario N2L 3G1, Canada.

出版信息

Org Lett. 2014 Nov 7;16(21):5748-51. doi: 10.1021/ol502811j. Epub 2014 Oct 22.

Abstract

The conjugate alkynylation of alkylidene Meldrum's acids with alkynylalanes and alkynyl Grignards allows for the formation of propargylic all-carbon quaternary stereocenters in high yields. Ag2CO3-catalyzed intramolecular cyclization of propargylic Meldrum's acid derivatives offers a two-step entry into complex γ-alkylidene butyrolactones containing an all-carbon quaternary center at the C-4 position.

摘要

偕二炔基 Meldrum's 酸与炔丙基丙氨酸和炔基格氏试剂的共轭炔基化反应能够以高产率形成丙炔基全碳季立体中心。Ag2CO3 催化的丙炔基 Meldrum's 酸衍生物的分子内环化提供了两步法进入含有全碳季立体中心的 C-4 位的复杂γ-亚烷基丁内酯。