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

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Title: Nickel-catalyzed dimerization of pyrrolidinoindoline scaffolds: systematic access to chimonanthines, folicanthines and (+)-WIN 64821
Authors: Wada, Mitsuhiro Browse this author
Murata, Takahisa Browse this author →KAKEN DB
Oikawa, Hideaki Browse this author →KAKEN DB
Oguri, Hiroki Browse this author →KAKEN DB
Issue Date: 14-Jan-2014
Publisher: Royal Society of Chemistry
Journal Title: Organic & biomolecular chemistry
Volume: 12
Issue: 2
Start Page: 298
End Page: 306
Publisher DOI: 10.1039/c3ob41918e
PMID: 24217772
Abstract: 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.
Type: article (author version)
URI: http://hdl.handle.net/2115/57769
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 大栗 博毅

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