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 Jun 2018
Accepted
20 Jul 2018
First published
31 Jul 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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