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Practical and Robust Method for Regio- and Stereoselective Preparation of (E)-Ketene tert-Butyl TMS Acetals and β-Ketoester-derived tert-Butyl (1Z,3E)-1,3-Bis(TMS)dienol Ethers

Tomohito Okabayashi, Akira Iida, Kenta Takai, Yuuya Nawate, Tomonori Misaki and Yoo Tanabe*

*Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan, Email: tanabekwansei.ac.jp

T. Okabayashi, A. Iida, K. Takai, Y. Nawate, T. Misaki, Y. Tanabe, J. Org. Chem., 2007, 72, 8142-8145.

DOI: 10.1021/jo701456t


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Abstract

An efficient, practical, robust method for the regio- and stereoselective preparation of ketene trimethylsilyl acetals derived from tert-butyl esters can be performed under convenient reaction conditions: LDA-TMSCl, 0-5 °C, and cyclopentyl methyl ether (CPME) as solvent. The stereocontrolled preparation of highly reactive β-ketoester-derived tert-butyl (1Z,3E)-1,3-bis(TMS)dienol ethers is also described.

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Key Words

Silyl Enol Ethers


ID: J42-Y2007-3400