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Molecules 2004, 9(5), 330-348; doi:10.3390/90500330

Masked ω-Lithio Ester Enolates: Synthetic Applications

Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
Author to whom correspondence should be addressed.
Received: 25 February 2004 / Accepted: 15 March 2004 / Published: 30 April 2004
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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 ortho esters 14: the β-chloro OBO ester derivate generates the γ- lactones 15 and the γ-chloro OBO ester gives corresponding esters 8.
Keywords: Chlorine-lithium exchange; functionalized ester; arene-catalyzed lithiation. Chlorine-lithium exchange; functionalized ester; arene-catalyzed lithiation.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Yus, M.; Torregrosa, R.; Pastor, I.M. Masked ω-Lithio Ester Enolates: Synthetic Applications. Molecules 2004, 9, 330-348.

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