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Lewis Acid-Catalyzed Alkylation of Azulene Derivatives with Epoxides and Oxetanes: A Regioselective Approach to Functionalized Azulene Alcohols

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Upon treatment with a catalytic amount of BF 3 ·OEt 2, the reaction between azulene derivatives and epoxides efficiently affords azulenylethanol derivatives. In most cases, this ring-opening transformation proceeds with high regioselectivity, favoring nucleophilic attack at the more substituted position of the epoxide. Stereochemical studies support an S N 2-type mechanism for the transformation. Furthermore, a preliminary investigation revealed that appropriately substituted oxetanes can also participate in this ring-opening reaction, delivering the corresponding homologated alcohols under similar catalytic conditions.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c02648

Authors: Gonzalo Brotons, Patricia García-Martínez, Olaya Bernardo, Luis A. López

Institutions: Universidad de Oviedo, ORFEO-CINQA Research Network

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Gobierno del Principado de Asturias, Ministerio de Ciencia e Innovación, European Regional Development Fund