Next Article in Journal / Special Issue
Polymer-Supported Cinchona Alkaloid-Derived Ammonium Salts as Recoverable Phase-Transfer Catalysts for the Asymmetric Synthesis of α-Amino Acids
Previous Article in Journal / Special Issue
1-Hydroxymethyl-4-phenylsulfonybutadiene, a Versatile Building Block for the Synthesis of 2,3,4-Trisusbtituted Tetrahydrothiophenes
Molecules 2004, 9(5), 330-348; doi:10.3390/90500330

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
Download PDF [235 KB, uploaded 18 June 2014]


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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
MDPI and ACS Style

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

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here


Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert