Issue 14, 2023
From the journal:

Organic & Biomolecular Chemistry

Stereoselective [2 + 2] photodimerization: a viable strategy for the synthesis of enantiopure cyclobutane derivatives†

Fabrizio Medici, ORCID logo a   Alessandra Puglisi, ORCID logo a   Sergio Rossi, ORCID logo a   Laura Raimondi ORCID logo a  and  Maurizio Benaglia ORCID logo *a  

* Corresponding authors

a Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi, 19, 20133 Milano, Italy
E-mail: maurizio.benaglia@unimi.it

Abstract

The [2 + 2] photodimerization of cinnamic acid derivatives to afford enantiopure cyclobutanes has been investigated. The use of a chiral auxiliary represents a convenient and straightforward method to exert enantiocontrol on the reaction. By exploiting Evans oxazolidinones, the stereoselective light-driven cyclisation affords a functionalised cyclobutane ring with up to 99% enantiocontrol after removing the chiral auxiliary. In-flow experiments allowed us to improve further the efficiency of the methodology, leading to high conversion and excellent enantioselectivity.

Graphical abstract: Stereoselective [2 + 2] photodimerization: a viable strategy for the synthesis of enantiopure cyclobutane derivatives

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Article information

DOI
https://doi.org/10.1039/D3OB00232B
Article type
Communication
Submitted
13 Feb 2023
Accepted
13 Mar 2023
First published
14 Mar 2023
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2023,21, 2899-2904

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Stereoselective [2 + 2] photodimerization: a viable strategy for the synthesis of enantiopure cyclobutane derivatives

F. Medici, A. Puglisi, S. Rossi, L. Raimondi and M. Benaglia, Org. Biomol. Chem., 2023, 21, 2899 DOI: 10.1039/D3OB00232B

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