Multinuclear Pd/Zn Complex-Catalyzed Asymmetric Alkylative Ring-Opening Reaction of Oxabicyclic Alkenes

A multinuclear palladium catalyst can be used to realize the efficient catalytic asymmetric alkylative ring-opening reaction of oxabicyclic alkenes using dimethylzinc. The use of (R)-BINOL-PHOS bearing bisphosphine and diol moieties is essential for achieving excellent catalytic performance; the cor...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 5; pp. 868 - 871
Main Authors Endo, Kohei, Tanaka, Keisuke, Ogawa, Mika, Shibata, Takanori
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.03.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANOZINC REAGENTS
LINKED-BINOL
ENANTIOSELECTIVITY
PHOSPHINE LIGAND
BIDENTATE
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Summary:A multinuclear palladium catalyst can be used to realize the efficient catalytic asymmetric alkylative ring-opening reaction of oxabicyclic alkenes using dimethylzinc. The use of (R)-BINOL-PHOS bearing bisphosphine and diol moieties is essential for achieving excellent catalytic performance; the corresponding monophosphine and hydroxy-protected derivatives showed lower catalytic activities and/or enantioselectivities. The generation of Pd/Zn-multinuclear complexes is a key feature of the present catalysis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol102928q