Use of X-ray diffraction data in stereochemical studies of (−)-menthone reactions with aromatic aldehydes

X-ray diffraction analysis proved that the stereochemical configuration of interaction products of (−)-menthone with aromatic aldehydes (α,β-unsaturated ketones or β-hydroxyketones) depends on the generation conditions of intermediate enolate carbanions. In irreversible deprotonation of (−)-menthone with strong sterically hindered organometallic bases, products of interaction with aldehydes preserve the 1R,4S-configuration; in equilibrium conditions, 1R,4R-diastereomers of the corresponding α,β-unsaturated ketones are formed with high stereoselectivity. Institute of Single Crystals, Academy of Sciences of Ukrainian Republic. Translated fromZhurnal Strukturnoi Khimii, Vol. 35, No. 5, pp. 133–142, September–October, 1994. Translated by T. Yudanova