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Diastereoselective C-H carbonylative annulation of aliphatic amines: a rapid route to functionalized ?-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.

SUBMITTER: Png ZM

PROVIDER: S-EPMC6182607 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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

Png Zhuang Mao ZM Cabrera-Pardo Jaime R JR Peiró Cadahía Jorge J Gaunt Matthew J MJ

Chemical science 20180731 39

A palladium(ii)-catalysed C(sp<sup>3</sup>)-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. ...[more]

PMID: 30393523

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