Next Article in Journal
Next Article in Special Issue
Previous Article in Journal
Previous Article in Special Issue
Molecules 2004, 9(5), 330-348; doi:10.3390/90500330
Article

Masked ω-Lithio Ester Enolates: Synthetic Applications

* ,  and
Received: 25 February 2004; Accepted: 15 March 2004 / Published: 30 April 2004
Download PDF [235 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

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

AMA Style

Yus M, Torregrosa R, Pastor IM. Masked ω-Lithio Ester Enolates: Synthetic Applications. Molecules. 2004; 9(5):330-348.

Chicago/Turabian Style

Yus, Miguel; Torregrosa, Rosario; Pastor, Isidro M. 2004. "Masked ω-Lithio Ester Enolates: Synthetic Applications." Molecules 9, no. 5: 330-348.



Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert