Nickel-catalyzed dimerization of pyrrolidinoindoline scaffolds: systematic access to chimonanthines, folicanthines and (+)-WIN 64821

Wada, Mitsuhiro; Murata, Takahisa; Oikawa, Hideaki; Oguri, Hiroki

Nickel-catalyzed dimerization of pyrrolidinoindoline scaffolds: systematic access to chimonanthines, folicanthines and (+)-WIN 64821

Wada, Mitsuhiro; Murata, Takahisa; Oikawa, Hideaki et al.

Organic & biomolecular chemistry, 2014, 12(2), 298-306

Permalink : https://hdl.handle.net/2115/57769

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アクセス権	open access
URI	https://hdl.handle.net/2115/57769
タイトル	Nickel-catalyzed dimerization of pyrrolidinoindoline scaffolds: systematic access to chimonanthines, folicanthines and (+)-WIN 64821
著者	Wada, Mitsuhiro ; Murata, Takahisa ; Oikawa, Hideaki ; Oguri, Hiroki
著者名 Wada, Mitsuhiro
e-Rad_Researcher 40422365 著者名 Murata, Takahisa
e-Rad_Researcher 00185175 著者名 Oikawa, Hideaki
e-Rad_Researcher 80311546 著者名 Oguri, Hiroki
言語	英語
発行日	2014-01-14
出版者	Royal Society of Chemistry
収録物名	Organic & biomolecular chemistry
巻(号)	12(2)
ページ	298-306
抄録	While metal-promoted activation of tertiary alkyl halides often causes elimination and hydrodehalogenation, we have developed a nickel-catalyzed reductive dimerization that allows the generation of a potently reactive tertiary radical equivalent to form a very congested C(sp(3))-C(sp(3)) bond even below room temperature. The catalytic protocol is applicable to the dimerization of several pyrrolidinoindoline scaffolds through an appropriate choice of catalyst to accommodate different substrate reactivities with functional group compatibilities. The efficiency of the nickel-catalyzed protocol was successfully demonstrated through a systematic total synthesis of chimonanthines, folicanthines and (+)-WIN 64821.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
PISSN	1477-0520
EISSN	1477-0539
関連情報	PMID 24217772
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1039/c3ob41918e