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

Nakamura, Shogo; Nishino, Soshi; Hirano, Koji

doi:https://doi.org/10.1021/acs.joc.2c02632

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

アクセス数:334件（2025-08-28 17:22 集計）

固定URL: https://hdl.handle.net/11094/92683

閲覧可能ファイル

ファイル	フォーマット	利用条件	サイズ	閲覧回数	利用開始日	説明	information
JOrgChem_88_2_1270	pdf	なし	702 KB	93	2024.01.20

論文情報

ファイル出力 EndNote Basic出力 Mendeley出力

タイトル	Synthesis of α-Aminophosphonates by Umpolung-Enabled Cu-Catalyzed Regioselective Hydroamination
著者	著者名 Nakamura, Shogo
	著者名 Nishino, Soshi
	NRID 1000070532696 1000070532696 ORCID 0000-0001-9752-1985 0000-0001-9752-1985 researchmap permalink koj koj Scopus Author ID 7402407063 7402407063 著者名 Hirano, Koji
内容	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.
抄録	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.
出版者	American Chemical Society
収録物名	Journal of Organic Chemistry
巻(号)	88(2)
ページ	1270-1281
刊行年月	2023-01-20
言語	英語
ハンドルURL	https://hdl.handle.net/11094/92683
PISSN	00223263
eISSN	15206904
関連情報 (isVersionOf)	DOI (出版社版) https://doi.org/10.1021/acs.joc.2c02632
アクセス権	open access
権利情報	© 2023 American Chemical Society.
権利情報	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.
出版タイプ	Accepted Manuscript
カテゴリ	学術雑誌論文 Journal Article

資源タイプ	学術雑誌論文
ローカル資源タイプ	学術雑誌論文
DCMI資源タイプ	text
DCTERMS.bibliographicCitation	Journal of Organic Chemistry. 2023, 88(2), p. 1270-1281
DC.title	Synthesis of α-Aminophosphonates by Umpolung-Enabled Cu-Catalyzed Regioselective Hydroamination
DC.creator	Nakamura, Shogo
	Nishino, Soshi
	Hirano, Koji
DC.publisher	American Chemical Society
DC.language' scheme='DCTERMS.RFC1766	英語
DC.type' scheme='DCTERMS.DCMIType	text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2023-01-20
DC.identifier	https://doi.org/10.1021/acs.joc.2c02632
DC.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.
DCTERMS.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.
DC.rights	© 2023 American Chemical Society.
DC.rights	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.
DC.format	92683
citation_title	Synthesis of α-Aminophosphonates by Umpolung-Enabled Cu-Catalyzed Regioselective Hydroamination
citation_author	Nakamura, Shogo
	Nishino, Soshi
	Hirano, Koji
citation_publisher	American Chemical Society
citation_language	英語
citation_date	2023-01-20
citation_journal_title	Journal of Organic Chemistry
citation_volume	88
citation_issue	2
citation_firstpage	1270
citation_lastpage	1281
citation_doi	https://doi.org/10.1021/acs.joc.2c02632
citation_public_url	https://hdl.handle.net/11094/92683

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

閲覧可能ファイル

論文情報

論文詳細を表示