通过钯催化的碳酰胺化反应立体选择性合成六氢-3H-吡咯并[3,2-b]吡咯-3-酮。

Diastereoselective synthesis of hexahydro-3H-pyrrolyzin-3-ones through Pd-catalyzed carboamination.

机构信息

Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, 06123 Perugia, Italy.

出版信息

J Org Chem. 2010 Mar 19;75(6):2134-7. doi: 10.1021/jo1002032.

DOI:10.1021/jo1002032

PMID:20170089

Abstract

The reaction of readily available (5R)-5-but-3-en-1-ylpyrrolidin-2-one with aryl bromides, chlorides, or triflates in the presence of Pd(2)(dba)(3), Xphos, and Cs(2)CO(3) in 1,4-dioxane at 120 degrees C affords (5R,7aR)-5-aryl hexahydropyrrolizidin-3-ones in good to high yields through a diastereoselective carboamination reaction. Aryl iodides are less successful substrates than bromides and chlorides.

摘要

(5R)-5-丁-3-烯基-2-吡咯烷酮与芳基溴化物、氯化物或三氟甲磺酸酯在 Pd(2)(dba)(3)、Xphos 和 Cs(2)CO(3)的存在下，于 120°C 的 1,4-二氧六环中反应，通过非对映选择性碳氨基化反应得到高产率至高收率的(5R,7aR)-5-芳基六氢吡咯烷-3-酮。芳基碘化物的反应性不如溴化物和氯化物。