Issue 22, 2004
From the journal:

Organic & Biomolecular Chemistry

Sequential hydroformylation/aldol reactions: versatile and controllable access to functionalised carbocycles from unsaturated carbonyl compounds

Mark D. Keränen,a   Kinga Kot,a   Christoph Hollmanna  and  Peter Eilbracht*a  

* Corresponding authors

a Fachbereich Chemie, Organische Chemie I, Universität Dortmund, Otto-Hahn-Str. 6, Dortmund, Germany
E-mail: peter.eilbracht@udo.edu
Fax: +49(0)231 755 5363
Tel: +49(0)231 755 3857

Abstract

Three different modes of hydroformylation/aldol reaction sequences involving either acid-catalysed aldol reactions, Mukaiyama aldol addition of pre-formed enolsilanes or aldol addition of in situ generated boron enolates can be applied to unsaturated ketones and ketoesters to afford the corresponding carbocyclic aldol adducts in good yields proceeding through the intermediate activated ketoaldehydes. In selected cases, complimentary, synthetically useful diastereoselectivities were observed in the products.

Graphical abstract: Sequential hydroformylation/aldol reactions: versatile and controllable access to functionalised carbocycles from unsaturated carbonyl compounds

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Article information

DOI
https://doi.org/10.1039/B410718G
Article type
Paper
Submitted
16 Jul 2004
Accepted
13 Sep 2004
First published
11 Oct 2004

Org. Biomol. Chem., 2004,2, 3379-3384

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Sequential hydroformylation/aldol reactions: versatile and controllable access to functionalised carbocycles from unsaturated carbonyl compounds

M. D. Keränen, K. Kot, C. Hollmann and P. Eilbracht, Org. Biomol. Chem., 2004, 2, 3379 DOI: 10.1039/B410718G

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