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

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

References

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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.