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

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Authors
Png, Zhuang Mao
Cabrera-Pardo, Jaime R
Peiró Cadahía, Jorge
  Gaunt, Matthew
Publication Date
2018-10-21
Journal Title
Chem Sci
ISSN
2041-6520
Publisher
Royal Society of Chemistry (RSC)
Volume
9
Issue
39
Pages
7628-7633
Language
eng
Type
Article
Physical Medium
Electronic-eCollection
Metadata
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Citation
Png, Z. M., Cabrera-Pardo, J. R., Peiró Cadahía, J., & Gaunt, M. (2018). Diastereoselective C-H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams.. Chem Sci, 9 (39), 7628-7633. https://doi.org/10.1039/c8sc02855a
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.
Sponsorship
EPSRC (EP/N031792/1) Royal Society (Wolfson Award) Agency for Science Technology and Research (A*STAR, Singapore) H2020-MSCA for an International Incoming Fellowship
Funder references
Engineering and Physical Sciences Research Council (EP/N031792/1)
The Royal Society (wm140104)
European Commission (655856)
Identifiers
External DOI: https://doi.org/10.1039/c8sc02855a
This record's URL: https://www.repository.cam.ac.uk/handle/1810/285642
Rights
Attribution 4.0 International
Licence URL: https://creativecommons.org/licenses/by/4.0/
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Attribution 4.0 International
Except where otherwise noted, this item's licence is described as Attribution 4.0 International