Issue 21, 2003
From the journal:

Organic & Biomolecular Chemistry

Scope of the reductive aldol reaction: application to aromatic carbocycles and heterocycles†

Timothy J. Donohoe,*a   David Housea  and  K. W. Aceb  

* Corresponding authors

a Dyson Perrins Laboratory, South Parks Road, Oxford, UK
E-mail: timothy.donohoe@chem.ox.ac.uk

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

Abstract

The reductive aldol reaction of electron deficient aromatic compounds has been investigated and found to be a viable method for carbon–carbon bond formation. Reductions under ammonia and ammonia-free conditions were both capable of facilitating the aldol reaction although the latter showed more scope for reaction with enolisable aldehydes. Moreover, reduction under ammonia-free conditions allowed the addition of Lewis acids which improved stereoselectivity to favour the anti stereoisomer. Production of the syn diastereoisomer was possible through either one of two different protocols performed after partial reduction was complete. While the main emphasis of this paper concerns the reductive aldol reaction of electron deficient pyrroles, it was also shown that both benzenoid and furan aromatic compounds were amenable to such reducing conditions.

Graphical abstract: Scope of the reductive aldol reaction: application to aromatic carbocycles and heterocycles

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Article information

DOI
https://doi.org/10.1039/B306937K
Article type
Paper
Submitted
17 Jun 2003
Accepted
30 Jul 2003
First published
12 Sep 2003

Org. Biomol. Chem., 2003,1, 3749-3757

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Scope of the reductive aldol reaction: application to aromatic carbocycles and heterocycles

T. J. Donohoe, D. House and K. W. Ace, Org. Biomol. Chem., 2003, 1, 3749 DOI: 10.1039/B306937K

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