Issue 23, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis and characterisation of a suite of four chiral pyridyl alcohols derived from (−)-menthol

Desmond Cunningham,b   Eva T. Gallagher,a   David H. Grayson,*a   Patrick J. McArdle,†b   Christina B. Storeya  and  Deborah J. Wilcocka  

* Corresponding authors

a Centre for Synthesis and Chemical Biology, University Chemical Laboratory, Trinity College, Dublin 2, Ireland

b Department of Chemistry, University College, Galway, Ireland

Abstract

Reaction of menthylmagnesium chloride with pyridine-2-carbaldehyde gives a mixture of four isomeric chiral menthyl- and neomenthyl-substituted pyridylcarbinols which were fully characterised by a combination of spectroscopic and X-ray crystallographic methods. All of these alcohols catalyse the addition of diethylzinc to benzaldehyde, but with disappointing enantioselectivities.

Graphical abstract: Synthesis and characterisation of a suite of four chiral pyridyl alcohols derived from (−)-menthol

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Article information

DOI
https://doi.org/10.1039/B205872N
Article type
Paper
Submitted
18 Jun 2002
Accepted
26 Sep 2002
First published
04 Nov 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2692-2698

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Synthesis and characterisation of a suite of four chiral pyridyl alcohols derived from (−)-menthol

D. Cunningham, E. T. Gallagher, D. H. Grayson, P. J. McArdle, C. B. Storey and D. J. Wilcock, J. Chem. Soc., Perkin Trans. 1, 2002, 2692 DOI: 10.1039/B205872N

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