Issue 20, 2009
From the journal:

Organic & Biomolecular Chemistry

Iron(III) chloride-catalysed direct nucleophilic α-substitution of Morita-Baylis-Hillman alcohols with alcohols, arenes, 1,3-dicarbonyl compounds, and thiols†

Xiaoxiang Zhang,a   Weidong Rao,a   Sallya  and  Philip Wai Hong Chan*a  

* Corresponding authors

a Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, Singapore
E-mail: waihong@ntu.edu.sg

Abstract

A general and efficient direct method for the α-substitution of Morita-Baylis-Hillman alcohols with carbon- and heteroatom-centred nucleophiles such as alcohols, arenes, 1,3-dicarbonyl compounds, and thiols in the presence of FeCl3·6H2O as catalyst has been developed. The reaction is operationally straightforward, accomplished in good to excellent product yields (40–99%) and with exclusive α-regioselectivity under mild conditions that did not need an inert and moisture-free environment.

Graphical abstract: Iron(III) chloride-catalysed direct nucleophilic α-substitution of Morita-Baylis-Hillman alcohols with alcohols, arenes, 1,3-dicarbonyl compounds, and thiols

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Article information

DOI
https://doi.org/10.1039/B908447A
Article type
Paper
Submitted
29 Apr 2009
Accepted
30 Jun 2009
First published
31 Jul 2009

Org. Biomol. Chem., 2009,7, 4186-4193

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Iron(III) chloride-catalysed direct nucleophilic α-substitution of Morita-Baylis-Hillman alcohols with alcohols, arenes, 1,3-dicarbonyl compounds, and thiols

X. Zhang, W. Rao, Sally and P. W. H. Chan, Org. Biomol. Chem., 2009, 7, 4186 DOI: 10.1039/B908447A

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