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Synthesis 2007(14): 2125-2134  
DOI: 10.1055/s-2007-983746
PAPER
© Georg Thieme Verlag Stuttgart · New York

Simple and Effective Protocol for Claisen-Schmidt Condensation of Hindered Cyclic Ketones with Aromatic Aldehydes

Valeriy Vashchenko*, Lidiya Kutulya, Alexander Krivoshey
STC ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, Lenin Avenue 60, Kharkov 61001, Ukraine
Fax: +38(057)3409343; e-Mail: valeravv@isc.kharkov.com;
Further Information

Publication History

Received 9 January 2007
Publication Date:
03 July 2007 (online)

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Abstract

A simple and effective methodology for Claisen-Schmidt condensation of (-)-menthone and other hindered cyclic ketones with aromatic aldehydes under highly basic conditions using a polar aprotic solvent and a strong base (alkali metal hydroxide or an alkoxide) is described and discussed.

Key words

aldehydes - α,β-unsaturated ketones - condensation - diastereoselectivity­ - super basic conditions

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30

Atom coordinates, crystallographic parameters, and full set of bond lengths and valence angles for the structure are deposited in Cambridge Crystallographic Data Centre (CCDC 645484); detailed analysis of the structure features for this compound will be published elsewhere.

46

For compound 3a, reference 18a gives only an 80 MHz 1H NMR spectrum in CCl4.