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

被引：29

作者：

Okabayashi, Tomohito ^{[1
]}

Iida, Akira ^{[1
]}

Takai, Kenta ^{[1
]}

Nawate, Yuuya ^{[1
]}

Misaki, Tomonori ^{[1
]}

Tanabe, Yoo ^{[1
]}

机构：

[1] Kwansei Gakuin Univ, Sch Sci & Technol, Dept Chem, Sanda, Hyogo 6691337, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 21期

关键词：

D O I：

10.1021/jo701456t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 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 degrees C, and cyclopentyl methyl ether (CPME) solvent. Two kinds of (Z)- and (E)-KSAs derived from (x-oxygen and (alpha-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) beta-ketoester-derived tert-butyl (1Z,3E)-1,3-bis(TMS)dienol ethers 2.

引用

页码：8142 / 8145

页数：4