Cyclopropanation of Strained Alkenes by Palladium-Catalyzed Reaction of 3-Trimethylsilyl- or 3-Pinacolatoboryl-1-arylallyl Acetates

The palladium‐catalyzed cyclopropanation of strained alkenes with 3‐trimethylsilyl‐ or 3‐pinacolatoboryl‐1‐arylallyl acetate derivatives is described. This reaction gives cyclopropanation products in good to high yields with a single diastereomer, and the key step is likely to involve the formation...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2012-03, Vol.354 (5), p.828-834
Main Authors: Horino, Yoshikazu, Homura, Naoki, Inoue, Kana, Yoshikawa, Saori
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
allylsilanes
Chemistry
cyclopropanation
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Organometalloidal and organometallic compounds
palladacyclobutenes
palladium carbenoids
Preparations and properties
Reactivity and mechanisms
Si derivatives
π-allylpalladium species
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Description
Summary:The palladium‐catalyzed cyclopropanation of strained alkenes with 3‐trimethylsilyl‐ or 3‐pinacolatoboryl‐1‐arylallyl acetate derivatives is described. This reaction gives cyclopropanation products in good to high yields with a single diastereomer, and the key step is likely to involve the formation of a palladacyclobutene complex from the α‐trimethylsilyl‐ or α‐pinacolatoboryl‐σ‐allylpalladium complex.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201100806