Issue 15, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Partial reduction of 3-heteroatom substituted 2-furoic acids: the role of an ortho group in viability and stereoselectivity

Timothy J. Donohoe,*a   Andrew A. Calabrese,ab   Jean-Baptiste Guillermin,b   Christopher. S. Frampton †c  and  Daryl Walterc  

* Corresponding authors

a Dyson Perrins Laboratory, South Parks Road, Oxford, UK
E-mail: timothy.donohoe@chem.ox.ac.uk
Fax: +(44) 01865 275674
Tel: +(44) 01865 275649

b Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK

c Department of Chemistry, Roche Discovery Welwyn, Broadwater Road, Welwyn Garden City, Herts, UK

Abstract

The synthesis of 2-furoic acid derivatives containing both 3-methoxy and 3-TMS groups is described. Reductive alkylation proceeded well to give us access to a series of highly functionalised dihydrofurans with potential for further elaboration. Of the two groups tested at C-3, the TMS derivative was found to be the more useful and gave rise to high levels of stereoselectivity when attached to a furan bearing a chiral auxiliary at C-2. A modification of the reaction conditions was made which enabled the TMS group to be cleaved during the reduction reaction without loss of stereoselectivity. Finally, it was also shown that the chiral auxiliary could be removed under acidic conditions to form 2-alkyl-3-TMS substituted dihydrofurans with excellent levels of enantiomeric purity.

Graphical abstract: Partial reduction of 3-heteroatom substituted 2-furoic acids: the role of an ortho group in viability and stereoselectivity

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Article information

DOI
https://doi.org/10.1039/B203437A
Article type
Paper
Submitted
09 Apr 2002
Accepted
07 Jun 2002
First published
28 Jun 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1748-1756

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Partial reduction of 3-heteroatom substituted 2-furoic acids: the role of an ortho group in viability and stereoselectivity

T. J. Donohoe, A. A. Calabrese, J. Guillermin, Christopher. S. Frampton and D. Walter, J. Chem. Soc., Perkin Trans. 1, 2002, 1748 DOI: 10.1039/B203437A

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