Issue 39, 2018

Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams

Abstract

A palladium(II)-catalysed C(sp3)–H carbonylation of free(NH) secondary aliphatic amines to 2-pyrrolidinones is described. A correlation between the nature of the carboxylate ligand and the diastereoselectivity and yield of the process was observed. As such, under these optimal conditions a range of aliphatic amines were converted to the corresponding trans-4,5-disubstituted 2-pyrrolidines with good d.r. and yield.

Graphical abstract: Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams

Supplementary files

Article information

Article type
Edge Article
Submitted
28 6 2018
Accepted
20 7 2018
First published
31 7 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 7628-7633

Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams

Z. M. Png, J. R. Cabrera-Pardo, J. Peiró Cadahía and M. J. Gaunt, Chem. Sci., 2018, 9, 7628 DOI: 10.1039/C8SC02855A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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