anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters

Nishino, Soshi; Nishii, Yuji; Hirano, Koji

doi:https://doi.org/10.1039/d2sc06003e

anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters

Nishino, Soshi; Nishii, Yuji; Hirano, Koji

Chemical Science, 2022, 13(48), 14387-14394

Number of Access:490（2025-07-17 21:10 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92608

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Title	anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters
Creator	CreatorName Nishino, Soshi
	NRID 1000070773787 1000070773787 ORCID 0000-0002-6824-0639 0000-0002-6824-0639 researchmap permalink y_nishii y_nishii Scopus Author ID 55233363700 55233363700 CreatorName Nishii, Yuji
	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	Nishino S., Nishii Y., Hirano K.. anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters. Chemical Science 13, 14387 (2022); https://doi.org/10.1039/d2sc06003e.
Abstract	A copper-catalysed regio- and diastereoselective borylamination of α,β-unsaturated esters with B2pin2 and hydroxylamines has been developed to deliver acyclic β-boryl-α-amino acid derivatives with high anti-diastereoselectivity (up to >99 : 1), which is difficult to obtain by the established methods. A chiral phosphoramidite ligand also successfully induces the enantioselectivity, giving the optically active β-borylated α-amino acids. The products can be stereospecifically transformed into β-functionalised α-amino acids, which are of potent interest in medicinal chemistry.
Publisher	Royal Society of Chemistry
Source Title	Chemical Science
Volume (Issue)	13(48)
Page	14387-14394
Date of Issued	2022-11-24
Language	English
Handle URL	https://hdl.handle.net/11094/92608
PISSN	20416520
eISSN	20416539
NCID	AA12555653
Relation.isIdenticalTo	DOI (Publisher Version) https://doi.org/10.1039/d2sc06003e
Access Rights	open access
CopyRight	This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
oaire:version	Version of Record
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCMI Type	Text
DCTERMS.bibliographicCitation	Chemical Science. 2022, 13(48), p. 14387-14394
DC.title	anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters
DC.creator	Nishino, Soshi
	Nishii, Yuji
	Hirano, Koji
DC.publisher	Royal Society of Chemistry
DC.language' scheme='DCTERMS.RFC1766	English
DC.type' scheme='DCTERMS.DCMIType	Text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2022-11-24
DC.identifier	https://doi.org/10.1039/d2sc06003e
DC.description	Nishino S., Nishii Y., Hirano K.. anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters. Chemical Science 13, 14387 (2022); https://doi.org/10.1039/d2sc06003e.
DCTERMS.abstract	A copper-catalysed regio- and diastereoselective borylamination of α,β-unsaturated esters with B2pin2 and hydroxylamines has been developed to deliver acyclic β-boryl-α-amino acid derivatives with high anti-diastereoselectivity (up to >99 : 1), which is difficult to obtain by the established methods. A chiral phosphoramidite ligand also successfully induces the enantioselectivity, giving the optically active β-borylated α-amino acids. The products can be stereospecifically transformed into β-functionalised α-amino acids, which are of potent interest in medicinal chemistry.
DC.rights	This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
DC.format	92608
citation_title	anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters
citation_author	Nishino, Soshi
	Nishii, Yuji
	Hirano, Koji
citation_publisher	Royal Society of Chemistry
citation_language	English
citation_date	2022-11-24
citation_journal_title	Chemical Science
citation_volume	13
citation_issue	48
citation_firstpage	14387
citation_lastpage	14394
citation_doi	https://doi.org/10.1039/d2sc06003e
citation_public_url	https://hdl.handle.net/11094/92608

anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters

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