CO2-Assisted Stereocontrolled Multi-Component Coupling Reactions Promoted by Ni-Catalytic System

A combination of Ni-catalyst and PPh3 promotes the three-component coupling reaction of vinyl epoxide, alkyne, and dimethylzinc under a carbon dioxide atmosphere to provide 2,5-heptadienyl alcohols with excellent E-stereoselectivity. The stereochemistry of the products from the multi-component coupl...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 11; no. 10
Main Authors Mori, Takamichi, Noba, Nao, Munakata, Miho, Kimura, Masanari
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.10.2022
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
carbon dioxide
3-COMPONENT SYNTHESIS
dimethylzinc
ALDEHYDES
STEREOSELECTIVE CYCLIZATION
vinyl epoxide
ALLYL ELECTROPHILES
nickel catalyst
NICKEL
UNACTIVATED PRIMARY
2+2 CYCLOADDITION
CARBOXYLATION
multi-component coupling reaction
CARBON-DIOXIDE
SELECTIVE FORMATION
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Summary:A combination of Ni-catalyst and PPh3 promotes the three-component coupling reaction of vinyl epoxide, alkyne, and dimethylzinc under a carbon dioxide atmosphere to provide 2,5-heptadienyl alcohols with excellent E-stereoselectivity. The stereochemistry of the products from the multi-component coupling reaction is controlled via an oxanickelacycle intermediate, which is formed by the insertion of carbon dioxide.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202200232