Synthesis of α-Aminophosphonates by Umpolung-Enabled Cu-Catalyzed Regioselective Hydroamination

Nakamura, Shogo; Nishino, Soshi; Hirano, Koji

Journal of Organic Chemistry, 2023, 88(2), 1270-1281

Number of Access:316（2025-07-17 20:26 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92683

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Title
Synthesis of α-Aminophosphonates by Umpolung-Enabled Cu-Catalyzed Regioselective Hydroamination
Creator
CreatorName
Nakamura, Shogo
CreatorName
Nishino, Soshi
NRID
1000070532696 1000070532696
ORCID
0000-0001-9752-1985 0000-0001-9752-1985
researchmap permalink
koj koj
Scopus Author ID
7402407063 7402407063
CreatorName
Hirano, Koji
Description
Nakamura S., Nishino S., Hirano K.. Synthesis of α-Aminophosphonates by Umpolung-Enabled Cu-Catalyzed Regioselective Hydroamination. Journal of Organic Chemistry. 88(2), 1270-1281, 20 January 2023; © 2023 American Chemical Society. https://doi.org/10.1021/acs.joc.2c02632.
Abstract
A copper-catalyzed regioselective hydroamination of α,β-unsaturated phosphonates has been developed to form corresponding α-aminophosphonates of interest in medicinal chemistry. The introduction of an umpolung, electrophilic amination strategy with the hydroxylamine derivative is the key to achieving the α-amination regioselectivity, which is otherwise difficult under the conventional nucleophilic hydroamination conditions with the parent amine. Asymmetric synthesis with a chiral bisphosphine ligand and application to a related silylamination reaction are also described.
Publisher
American Chemical Society
Source Title
Journal of Organic Chemistry
Volume (Issue)
88(2)
Page
1270-1281
Date of Issued
2023-01-20
Language
English
Handle URL
https://hdl.handle.net/11094/92683
PISSN
00223263
eISSN
15206904
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acs.joc.2c02632
Access Rights
open access
CopyRight
© 2023 American Chemical Society.
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.2c02632.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article