Issue 45, 2013
From the journal:

Organic & Biomolecular Chemistry

Sulfur-assisted domino access to bicyclic dihydrofurans: case study and early synthetic applications†

Concetta Paolella,‡a   Daniele D'Alonzo,‡*a   Giovanni Palumboa  and  Annalisa Guaragna*a  

* Corresponding authors

a Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, via Cintia 21, I-80126 Napoli, Italy
E-mail: dandalonzo@unina.it, guaragna@unina.it
Fax: +39 081 674393
Tel: +39 081 674119

Abstract

A DDQ-mediated domino reaction (up to six steps in a single process) has been developed to selectively provide substituted dihydrofurans from a common starting material containing a cyclic bis-thioenol ether. Study of the reaction mechanism highlighted a role played by the sulfur-containing moiety in influencing reaction rate and stereoselectivity.

Graphical abstract: Sulfur-assisted domino access to bicyclic dihydrofurans: case study and early synthetic applications

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Article information

DOI
https://doi.org/10.1039/C3OB41324A
Article type
Communication
Submitted
27 Jun 2013
Accepted
10 Sep 2013
First published
13 Sep 2013

Org. Biomol. Chem., 2013,11, 7825-7829

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Sulfur-assisted domino access to bicyclic dihydrofurans: case study and early synthetic applications

C. Paolella, D. D'Alonzo, G. Palumbo and A. Guaragna, Org. Biomol. Chem., 2013, 11, 7825 DOI: 10.1039/C3OB41324A

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