Molecules

Masked ω-lithio ester enolates: synthetic applications

M Yus, R Torregrosa, IM Pastor

Index: Yus, Miguel; Torregrosa, Rosario; Pastor, Isidro M. Molecules, 2004 , vol. 9, # 5 p. 330 - 348

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Citation Number: 12

Abstract

Abstract: The protocol of lithiation by means of lithium and a catalytic (5% molar) amount of DTBB (4, 4'-di-tert-butylbiphenyl), applied to ω-chloro ortho ester 6 under Barbier-type conditions gives, after final acid-catalyzed methanolysis, the corresponding functionalized esters 8 or 9 (for chlorotrimethylsilane as electrophile) or, after ortho ester deprotection and acid catalyzed treatment, the δ-lactones 11. The procedure is also practical for bicyclic ...