Lipase‐Palladium Co‐catalyzed Dynamic Kinetic Resolution of Racemic Allylic Esters

Oono, Masato; Yamada, Akane; Kimura, Masanari; Kanomata, Kyohei; Akai, Shuji

doi:https://doi.org/10.1002/chem.202404406

Lipase‐Palladium Co‐catalyzed Dynamic Kinetic Resolution of Racemic Allylic Esters

Oono, Masato; Yamada, Akane; Kimura, Masanari et al.

Chemistry – A European Journal, 2025, e202404406

アクセス数:13件（2025-04-10 09:11 集計）

固定URL: https://hdl.handle.net/11094/100631

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
ChemistryAEuropeanJ_e202404406	pdf	なし	621 KB		2026.03.13

論文情報

ファイル出力 EndNote Basic出力 Mendeley出力

タイトル	Lipase‐Palladium Co‐catalyzed Dynamic Kinetic Resolution of Racemic Allylic Esters
著者	著者名 Oono, Masato
	著者名 Yamada, Akane
	NRID 1000010274622 1000010274622 著者名 Kimura, Masanari
	NRID 1000030880447 1000030880447 ORCID 0000-0002-2251-4665 0000-0002-2251-4665 researchmap permalink kyohei_kanomata kyohei_kanomata Scopus Author ID 39861733600 39861733600 著者名 Kanomata, Kyohei
	NRID 1000060192457 1000060192457 ORCID 0000-0001-9149-8745 0000-0001-9149-8745 researchmap permalink shuji_akai shuji_akai Scopus Author ID 7006001526 7006001526 著者名 Akai, Shuji
内容	This is the accepted version of the following article: Oono Masato, Yamada Akane, Kimura Masanari, et al. Lipase‐Palladium Co‐catalyzed Dynamic Kinetic Resolution of Racemic Allylic Esters. Chemistry – A European Journal, e202404406, which has been published in final form at https://doi.org/10.1002/chem.202404406. This article may be used for non-commercialpurposes in accordance with the Wiley Self-ArchivingPolicy [https://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html]
抄録	Dynamic kinetic resolution (DKR) by combining lipase-catalyzed esterification of racemic sec-alcohols and in situ racemization has been widely studied; however, reports on DKR involving lipase-catalyzed hydrolysis of racemic esters are scarce. This problem is probably due to the lack of more effective and general racemization methods. Herein, we report the enhanced hydrolytic DKR of racemic allylic esters. The discovery of the monodentate ligand P[C6H3-2,6-(OMe)2]3, which in situ generates Pd complex(es) highly reactive to racemization and the NaOAc-mediated acceleration of racemization, are notable breakthroughs. Consequently, the DKR of racemic allylic esters can be completed in a few hours at 40 °C in most cases, yielding optically active allylic alcohols (93% to >99% ee) in 58%–91% isolated yields with minimal side reactions.
出版者	Wiley
収録物名	Chemistry – A European Journal
ページ	e202404406
刊行年月	2025-03-13
言語	英語
ハンドルURL	https://hdl.handle.net/11094/100631
PISSN	09476539
eISSN	15213765
関連情報 (isVersionOf)	DOI (出版社版) https://doi.org/10.1002/chem.202404406
アクセス権	embargoed access
権利情報	© 2025 Wiley-VCH GmbH
権利情報	The full-text file will be made open to the public on 13 March 2026 in accordance with the publisher's policy.
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
DCTERMS.bibliographicCitation	Chemistry – A European Journal. 2025, p. e202404406
DC.title	Lipase‐Palladium Co‐catalyzed Dynamic Kinetic Resolution of Racemic Allylic Esters
DC.creator	Oono, Masato
	Yamada, Akane
	Kimura, Masanari
	Kanomata, Kyohei
	Akai, Shuji
DC.publisher	Wiley
DC.language' scheme='DCTERMS.RFC1766	英語
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2025-03-13
DC.identifier	https://doi.org/10.1002/chem.202404406
DC.description	This is the accepted version of the following article: Oono Masato, Yamada Akane, Kimura Masanari, et al. Lipase‐Palladium Co‐catalyzed Dynamic Kinetic Resolution of Racemic Allylic Esters. Chemistry – A European Journal, e202404406, which has been published in final form at https://doi.org/10.1002/chem.202404406. This article may be used for non-commercialpurposes in accordance with the Wiley Self-ArchivingPolicy [https://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html]
DCTERMS.abstract	Dynamic kinetic resolution (DKR) by combining lipase-catalyzed esterification of racemic sec-alcohols and in situ racemization has been widely studied; however, reports on DKR involving lipase-catalyzed hydrolysis of racemic esters are scarce. This problem is probably due to the lack of more effective and general racemization methods. Herein, we report the enhanced hydrolytic DKR of racemic allylic esters. The discovery of the monodentate ligand P[C6H3-2,6-(OMe)2]3, which in situ generates Pd complex(es) highly reactive to racemization and the NaOAc-mediated acceleration of racemization, are notable breakthroughs. Consequently, the DKR of racemic allylic esters can be completed in a few hours at 40 °C in most cases, yielding optically active allylic alcohols (93% to >99% ee) in 58%–91% isolated yields with minimal side reactions.
DC.rights	© 2025 Wiley-VCH GmbH
DC.rights	The full-text file will be made open to the public on 13 March 2026 in accordance with the publisher's policy.
DC.format	100631
citation_title	Lipase‐Palladium Co‐catalyzed Dynamic Kinetic Resolution of Racemic Allylic Esters
citation_author	Oono, Masato
	Yamada, Akane
	Kimura, Masanari
	Kanomata, Kyohei
	Akai, Shuji
citation_publisher	Wiley
citation_language	英語
citation_date	2025-03-13
citation_journal_title	Chemistry – A European Journal
citation_firstpage	e202404406
citation_doi	https://doi.org/10.1002/chem.202404406
citation_public_url	https://hdl.handle.net/11094/100631

Lipase‐Palladium Co‐catalyzed Dynamic Kinetic Resolution of Racemic Allylic Esters

閲覧可能ファイル

論文情報

論文詳細を表示