Organic Chemistry Portal

Abstracts

Search:

Peterson Allenation Using (Z)-(1-Lithio-1-alkenyl)trimethylsilanes

Akira Tsubouchi, Takashiro Kira, Takeshi Takeda*

*Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan, Email: takeda-tcc.tuat.ac.jp

A. Tsubouchi, T. Kira, T. Takeda, Synlett, 2006, 2577-2580.

DOI: 10.1055/s-2006-951474


Abstract

Lithium alkoxides of β-silylallylic alcohols underwent the Peterson elimination in DMF to give allenes. A one pot process for a Peterson allenation reaction of carbonyl compounds using (Z)-(1-lithio-1-alkenyl)trimethylsilanes is described.

see article for more examples



Details

The document discusses the Peterson allenation using (Z)-(1-lithio-1-alkenyl)trimethylsilanes, a method developed by Akira Tsubouchi, Takashiro Kira, and Takeshi Takeda at Tokyo University of Agriculture and Technology. This method involves the Peterson elimination of lithium alkoxides derived from β-silylallylic alcohols in DMF to produce allenes. The process can also directly convert carbonyl compounds to allenes in a one-pot reaction using (Z)-(1-lithio-1-alkenyl)trimethylsilanes. The study highlights that using ether instead of THF for the preparation of lithium alkoxides results in better yields. The method offers an advantage over conventional two-step procedures by eliminating the need for additional transformations. The research also extends to the direct transformation of carbonyl compounds to allenes, utilizing (Z)-(1-lithio-1-alkenyl)trimethylsilanes generated via halogen-lithium exchange reactions. The document includes experimental details, reaction conditions, and yields for various substrates, demonstrating the method's efficiency and potential for synthesizing vinylallenes. The work was supported by the 21st Century COE program at Tokyo University of Agriculture and Technology.


Titanocene(II)-promoted carbonyl allenation utilizing 1,1-dichloroalk-1-enes

T. Shono, K. Ito, A. Tsubouchi, T. Takeda, Org. Biomol. Chem., 2005, 3, 2914-2916.


Key Words

alcohols, allenes, carbonyl, elimination, silicon, Peterson Olefination


ID: J60-Y2006-4660