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

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

Author information

1
Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, 06123 Perugia, Italy.

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.

PMID:
20170089
DOI:
10.1021/jo1002032
[Indexed for MEDLINE]

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