Toward Multi-Functionalized Organogermaniums: Diastereoselective Transformations of Germacycles Derived from Cheletropic Reactions of Boron-Substituted Butadienes with Ge(II) Salts

Nojima, Taishi; Izumi, Yugo; Konishi, Akihito; Yasuda, Makoto

doi:https://doi.org/10.1002/ejoc.202400960

Toward Multi-Functionalized Organogermaniums: Diastereoselective Transformations of Germacycles Derived from Cheletropic Reactions of Boron-Substituted Butadienes with Ge(II) Salts

Nojima, Taishi; Izumi, Yugo; Konishi, Akihito et al.

European Journal of Organic Chemistry, 2024, 27(48), e202400960

Number of Access:574（2025-10-09 08:17 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/98892

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Title	Toward Multi-Functionalized Organogermaniums: Diastereoselective Transformations of Germacycles Derived from Cheletropic Reactions of Boron-Substituted Butadienes with Ge(II) Salts
Creator	CreatorName Nojima, Taishi
	CreatorName Izumi, Yugo
	NRID 1000010756480 1000010756480 ORCID 0000-0002-3438-786X 0000-0002-3438-786X researchmap permalink a-koni a-koni Scopus Author ID 26324944100 26324944100 CreatorName Konishi, Akihito
	NRID 1000040273601 1000040273601 ORCID 0000-0002-6618-2893 0000-0002-6618-2893 researchmap permalink read0185253 read0185253 Scopus Author ID 7402645045 7402645045 CreatorName Yasuda, Makoto
Subject	Allylation
	Cheletropic reaction
	Diastereoselective
	Germacycle
	Organogermanium
Description	Nojima T., Izumi Y., Konishi A., et al. Toward Multi-Functionalized Organogermaniums: Diastereoselective Transformations of Germacycles Derived from Cheletropic Reactions of Boron-Substituted Butadienes with Ge(II) Salts. European Journal of Organic Chemistry 27, e202400960 (2024); https://doi.org/10.1002/ejoc.202400960.
Abstract	The field of organogermanium in chemistry has recently attracted attention. Thanks to the inherent features of germanium (Ge), introducing Ge-based substituents into organic frameworks has enhanced bioactivity and optoelectronic properties of molecules. Herein, the synthesis of multi-functionalized organogermaniums using Ge(II) salts is reported. The germacycles having an allylboron moiety, which is derived from the (4+1) cycloadditions of the butadienes bearing a boronic ester moiety with Ge(II) salts, can be applied to further allylboration of aldehydes with perfect diastereoselectivity. The obtained allylated adducts enable access to π-extended organogermaniums with the retention of the stereocenters.
Publisher	John Wiley and Sons Inc
Source Title	European Journal of Organic Chemistry
Volume (Issue)	27(48)
Page	e202400960
Date of Issued	2024-12-23
Language	English
Handle URL	https://hdl.handle.net/11094/98892
PISSN	1434193X
eISSN	10990690
Relation.isIdenticalTo	DOI (Publisher Version) https://doi.org/10.1002/ejoc.202400960
Access Rights	open access
CopyRight	This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
oaire:version	Version of Record
Category	学術雑誌論文 Journal Article

Resource Type	journal article
Local Type	Journal Article
DCTERMS.bibliographicCitation	European Journal of Organic Chemistry. 2024, 27(48), p. e202400960
DC.title	Toward Multi-Functionalized Organogermaniums: Diastereoselective Transformations of Germacycles Derived from Cheletropic Reactions of Boron-Substituted Butadienes with Ge(II) Salts
DC.creator	Nojima, Taishi
	Izumi, Yugo
	Konishi, Akihito
	Yasuda, Makoto
DC.publisher	John Wiley and Sons Inc
DC.language' scheme='DCTERMS.RFC1766	English
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-12-23
DC.identifier	https://doi.org/10.1002/ejoc.202400960
DC.subject	Allylation
	Cheletropic reaction
	Diastereoselective
	Germacycle
	Organogermanium
DC.description	Nojima T., Izumi Y., Konishi A., et al. Toward Multi-Functionalized Organogermaniums: Diastereoselective Transformations of Germacycles Derived from Cheletropic Reactions of Boron-Substituted Butadienes with Ge(II) Salts. European Journal of Organic Chemistry 27, e202400960 (2024); https://doi.org/10.1002/ejoc.202400960.
DCTERMS.abstract	The field of organogermanium in chemistry has recently attracted attention. Thanks to the inherent features of germanium (Ge), introducing Ge-based substituents into organic frameworks has enhanced bioactivity and optoelectronic properties of molecules. Herein, the synthesis of multi-functionalized organogermaniums using Ge(II) salts is reported. The germacycles having an allylboron moiety, which is derived from the (4+1) cycloadditions of the butadienes bearing a boronic ester moiety with Ge(II) salts, can be applied to further allylboration of aldehydes with perfect diastereoselectivity. The obtained allylated adducts enable access to π-extended organogermaniums with the retention of the stereocenters.
DC.rights	This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
DC.format	98892
citation_title	Toward Multi-Functionalized Organogermaniums: Diastereoselective Transformations of Germacycles Derived from Cheletropic Reactions of Boron-Substituted Butadienes with Ge(II) Salts
citation_author	Nojima, Taishi
	Izumi, Yugo
	Konishi, Akihito
	Yasuda, Makoto
citation_publisher	John Wiley and Sons Inc
citation_language	English
citation_date	2024-12-23
citation_journal_title	European Journal of Organic Chemistry
citation_volume	27
citation_issue	48
citation_firstpage	e202400960
citation_doi	https://doi.org/10.1002/ejoc.202400960
citation_public_url	https://hdl.handle.net/11094/98892

Toward Multi-Functionalized Organogermaniums: Diastereoselective Transformations of Germacycles Derived from Cheletropic Reactions of Boron-Substituted Butadienes with Ge(II) Salts

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