Diastereoselective C–H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams† †Electronic supplementary information (ESI) available: Experimental procedures, characterization data and kinetic details. CCDC 1850700–1850701. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc02855a

A palladium( ii )-catalysed C(sp 3 )–H carbonylation of free(NH) secondary aliphatic amines to 2-pyrrolidinones is described. A palladium( ii )-catalysed C(sp 3 )–H carbonylation of free(NH) secondary aliphatic amines to 2-pyrrolidinones is described. A correlation between the nature of the carboxyl...

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Published inChemical science (Cambridge) Vol. 9; no. 39; pp. 7628 - 7633
Main Authors Png, Zhuang Mao, Cabrera-Pardo, Jaime R., Peiró Cadahía, Jorge, Gaunt, Matthew J.
Format Journal Article
LanguageEnglish
Published Royal Society of Chemistry 31.07.2018
Subjects
Chemistry
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Summary:A palladium( ii )-catalysed C(sp 3 )–H carbonylation of free(NH) secondary aliphatic amines to 2-pyrrolidinones is described. A palladium( ii )-catalysed C(sp 3 )–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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc02855a