Issue 21, 2002
From the journal:

Chemical Communications

KeteneClaisen rearrangement of camphor-derived 1,3-oxathianes: complete control of tertiary and quaternary stereogenic centres†

Varinder K. Aggarwal,*a   Alessandra Lattanzib  and  Daniel Fuentesa  

* Corresponding authors

a School of Chemistry, University of Bristol, Bristol, UK
E-mail: v.aggarwal@bristol.ac.uk
Fax: +44 (0)117 929 8611

b Dipartimento di Chimica, Università di Salerno, Via S. Allende I, Baronissi, Salerno, Italy

Abstract

Dichloroketene reacts, via a [3,3]-sigmatropic rearrangement, with camphor-derived 1,3-oxathianes of α,β-unsaturated aldehydes to give macrocyclic thiolactones in high yield and with complete transfer of chirality. The rearrangement is stereospecific.

Graphical abstract: Ketene Claisen rearrangement of camphor-derived 1,3-oxathianes: complete control of tertiary and quaternary stereogenic centres

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Article information

DOI
https://doi.org/10.1039/B206857E
Article type
Communication
Submitted
16 Jul 2002
Accepted
16 Sep 2002
First published
01 Oct 2002

Chem. Commun., 2002, 2534-2535

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Ketene Claisen rearrangement of camphor-derived 1,3-oxathianes: complete control of tertiary and quaternary stereogenic centres

V. K. Aggarwal, A. Lattanzi and D. Fuentes, Chem. Commun., 2002, 2534 DOI: 10.1039/B206857E

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