Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters

Kobayashi, Toshimichi; Nishino, Soshi; Miura, Masahiro; Hirano, Koji

doi:https://doi.org/10.1021/acs.orglett.2c00309

Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters

Kobayashi, Toshimichi; Nishino, Soshi; Miura, Masahiro et al.

Organic Letters, 2022, 24(6), 1418-1422

アクセス数:473件（2025-08-14 20:38 集計）

固定URL: https://hdl.handle.net/11094/92693

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タイトル	Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters
著者	著者名 Kobayashi, Toshimichi
	著者名 Nishino, Soshi
	NRID 1000020183626 1000020183626 ORCID 0000-0001-8288-6439 0000-0001-8288-6439 researchmap permalink read0013936 read0013936 Scopus Author ID 7402799909 7402799909 著者名 Miura, Masahiro
	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	Kobayashi T., Nishino S., Miura M., et al. Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters. Organic Letters. 24(6), 1418-1422, (2022), 18 February 2022; © 2022 American Chemical Society. https://doi.org/10.1021/acs.orglett.2c00309.
抄録	A copper-catalyzed silylamination of α,β-unsaturated esters with silylboranes and hydroxylamines has been developed to afford the corresponding β-silyl-α-amino acid derivatives, which are of great interest in medicinal and pharmaceutical chemistry. Additionally, by using a suitable chiral bisphosphine ligand, the asymmetric induction is possible, delivering the optically active β-silyl-α-amino acids with synthetically acceptable diastereomeric ratios (55:45-82:18 dr) and high enantiomeric ratios (81:19-99:1 er).
出版者	American Chemical Society
収録物名	Organic Letters
巻(号)	24(6)
ページ	1418-1422
刊行年月	2022-02-18
言語	英語
ハンドルURL	https://hdl.handle.net/11094/92693
PISSN	15237060
eISSN	15237052
関連情報 (isVersionOf)	DOI (出版社版) https://doi.org/10.1021/acs.orglett.2c00309
アクセス権	open access
権利情報	© 2022 American Chemical Society
権利情報	This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in, Organic Letters, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.2c00309.
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	Organic Letters. 2022, 24(6), p. 1418-1422
DC.title	Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters
DC.creator	Kobayashi, Toshimichi
	Nishino, Soshi
	Miura, Masahiro
	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	2022-02-18
DC.identifier	https://doi.org/10.1021/acs.orglett.2c00309
DC.description	Kobayashi T., Nishino S., Miura M., et al. Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters. Organic Letters. 24(6), 1418-1422, (2022), 18 February 2022; © 2022 American Chemical Society. https://doi.org/10.1021/acs.orglett.2c00309.
DCTERMS.abstract	A copper-catalyzed silylamination of α,β-unsaturated esters with silylboranes and hydroxylamines has been developed to afford the corresponding β-silyl-α-amino acid derivatives, which are of great interest in medicinal and pharmaceutical chemistry. Additionally, by using a suitable chiral bisphosphine ligand, the asymmetric induction is possible, delivering the optically active β-silyl-α-amino acids with synthetically acceptable diastereomeric ratios (55:45-82:18 dr) and high enantiomeric ratios (81:19-99:1 er).
DC.rights	© 2022 American Chemical Society
DC.rights	This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in, Organic Letters, copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.2c00309.
DC.format	92693
citation_title	Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters
citation_author	Kobayashi, Toshimichi
	Nishino, Soshi
	Miura, Masahiro
	Hirano, Koji
citation_publisher	American Chemical Society
citation_language	英語
citation_date	2022-02-18
citation_journal_title	Organic Letters
citation_volume	24
citation_issue	6
citation_firstpage	1418
citation_lastpage	1422
citation_doi	https://doi.org/10.1021/acs.orglett.2c00309
citation_public_url	https://hdl.handle.net/11094/92693

Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters

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