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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

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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 tanabe@kwansei.ac.jp

J. Org. Chem., 2007, 72 (21), pp 8142–8145

DOI: 10.1021/jo701456t

Publication Date (Web): September 18, 2007

Section:

Aliphatic Compounds

Abstract

We developed an efficient, practical, robust method for the regio- and stereoselective preparation of (E)-ketene trimethylsilyl acetals (KSAs) derived from tert-butyl esters 1. The reaction was performed under convenient reaction conditions; LDA−TMSCl, 0−5 °C, and cyclopentyl methyl ether (CPME) solvent. Two kinds of (Z)- and (E)-KSAs derived from α-oxygen and α-nitrogen-substituted tert-butyl esters, respectively, were also obtained in good yield. The present protocol was successfully applied to a stereocontrolled preparation of useful, but highly reactive (less accessible) β-ketoester-derived tert-butyl (1Z,3E)-1,3-bis(TMS)dienol ethers 2.

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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Lithium Hexamethyldisilazide-Mediated Enolizations: Influence of Triethylamine on E/Z Selectivities and Enolate Reactivities
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Published In Issue October 12, 2007
Received July 18, 2007

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Note

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

Abstract

Citing Articles

An Enantioselective, Intermolecular α-Arylation of Ester Enolates To Form Tertiary Stereocenters

An Enantioselective, Intermolecular α-Arylation of Ester Enolates To Form Tertiary Stereocenters

Synthesis of Phototrappable Shape-Shifting Molecules for Adaptive Guest Binding

Synthesis of Phototrappable Shape-Shifting Molecules for Adaptive Guest Binding

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp³-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp³-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides

Lithium Hexamethyldisilazide-Mediated Enolizations: Influence of Triethylamine on E/Z Selectivities and Enolate Reactivities