Issue 1, 2025

LiTMP-LiBr complex-induced lateral lithiation and cross ester condensation: direct access to isocoumarins from 2-methoxy o-toluate esters

Abstract

A LiTMP-LiBr complex facilitates a novel cross-ester coupling of 2-methoxy o-toluate esters to directly yield isocoumarin without the formation of any carbonyl intermediate. Aggregation plays a pivotal role in driving proximity-induced lateral lithiation and expediting acylation. In addition to many natural product precursors, the synthesis of (+)- and (−)-lunatinins is shown.

Graphical abstract: LiTMP-LiBr complex-induced lateral lithiation and cross ester condensation: direct access to isocoumarins from 2-methoxy o-toluate esters

Supplementary files

Article information

Article type
Research Article
Submitted
09 Sep 2024
Accepted
16 Oct 2024
First published
18 Oct 2024
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2025,12, 173-178

LiTMP-LiBr complex-induced lateral lithiation and cross ester condensation: direct access to isocoumarins from 2-methoxy o-toluate esters

M. Rehman, S. Daimary, R. Madhusudhana and R. Goreti, Org. Chem. Front., 2025, 12, 173 DOI: 10.1039/D4QO01678E

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