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

Number of Access:461（2025-07-17 20:19 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92693

Link to primary information

File	Format	Terms of use	Size	Views	Date.Available	Description	information
OrgLett_24_6_1418	pdf	None	542 KB	104	2023.10.05

Item Information

Output File Export EndNote Basic Export Mendeley

Title	Synthesis of β-Silyl-α-amino Acid Derivatives by Cu-Catalyzed Regio- and Enantioselective Silylamination of α,β-Unsaturated Esters
Creator	CreatorName Kobayashi, Toshimichi
	CreatorName Nishino, Soshi
	NRID 1000020183626 1000020183626 ORCID 0000-0001-8288-6439 0000-0001-8288-6439 researchmap permalink read0013936 read0013936 Scopus Author ID 7402799909 7402799909 CreatorName Miura, Masahiro
	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	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.
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).
Publisher	American Chemical Society
Source Title	Organic Letters
Volume (Issue)	24(6)
Page	1418-1422
Date of Issued	2022-02-18
Language	English
Handle URL	https://hdl.handle.net/11094/92693
PISSN	15237060
eISSN	15237052
Relation.isVersionOf	DOI (Publisher Version) https://doi.org/10.1021/acs.orglett.2c00309
Access Rights	open access
CopyRight	© 2022 American Chemical Society
CopyRight	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.
oaire:version	Accepted Manuscript
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCMI Type	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	English
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	English
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

Link to primary information

Item Information

Show details