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

Masked ω-Lithio Ester Enolates: Synthetic Applications

* ,  and
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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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 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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