Access to Naphthoic Acid Derivatives through an Oxabenzonorbornadiene Rearrangement

Herein, the synthesis of 1-hydroxy-2-naphthoic acid esters through an unexpected Lewis-acid-mediated 1,2-acyl shift of oxabenzonorbornadienes is reported. Using this methodology, novel substitution patterns for 1-hydroxy-2-naphtoic acid esters can be obtained. A mechanistic proposal and rationale for this transformation, the products of which had been previously incorrectly characterized, is given.

Automated summary

Here, a synthesis method of 1-hydroxy-2-naphthoic acid esters through an unexpected Lewis-acid-mediated 1,2-acyl shift of oxabenzonorbornadienes is reported. This method allows the obtaining of novel substitution patterns for 1-hydroxy-2-naphtoic acid esters. A mechanistic proposal and rationale for this transformation, which had been previously incorrectly characterized, is provided.