ChemInform Abstract: General Method for Preparation of Allenic Zinc Reagents by Three- Carbon Homologation of Triorganozincates: Convergent Three-Component Coupling of Propargylic Substrates, Triorganozincates, and Electrophilic Reagents.
✍ Scribed by T. HARADA; T. KATSUHIRA; A. OSADA; K. IWAZAKI; K. MAEJIMA; A. OKU
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 35 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
General Method for Preparation of Allenic Zinc Reagents by Three-Carbon Homologation of Triorganozincates:
Convergent Three-Component Coupling of Propargylic Substrates, Triorganozincates, and Electrophilic Reagents.
-Allenic zinc reagents are prepared by reaction of propargylic substrates with a variety of triorganozincates. They undergo a subsequent coupling reaction with a variety of electrophiles (e.g. aldehydes) regioselectively at the γ-position to afford the corresponding propargylic derivatives. This is a general method for the three-carbon homologation reaction giving anti-homopropargylic alcohols. By using silicon-containing allenic zinc reagents, this method provides functionalized organosilicon compounds of high synthetic utility.