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

T Okabayashi, A Iida, K Takai, Y Nawate…

Index: Okabayashi, Tomohito; Iida, Akira; Takai, Kenta; Nawate, Yuuya; Misaki, Tomonori; Tanabe, Yoo Journal of Organic Chemistry, 2007 , vol. 72, # 21 p. 8142 - 8145

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Citation Number: 21

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 ...