ChemInform Abstract: New Homochiral Ketoalcohols from Aldol Reactions of (+)‐Isomenthone and Reversal of Diastereoselectivity.

Abstract

stereochemistry stereochemistry (general, optical resolution) O 0030 -022New Homochiral Ketoalcohols from Aldol Reactions of (+)-Isomenthone and Reversal of Diastereoselectivity.-Aldol reactions of the enolate derived from isomenthone (I) proceed with complete diastereoselectivity at C-6, but the stereochemical outcome of the attack on the aldehyde carbon is unexpectedly reversed by changing the reaction quenching temperature. -(CHUGHTAI, J. H.; GARDINER, J. M.; HARRIS, S. G.; PARSONS, S.; RANKIN, D. W. H.; SCHWALBE, C. H.; Tetrahedron Lett. 38 (1997) 52, 9043-9046; Dep. Chem., Univ. Manchester Inst. Sci. Technol., Manchester M60 1QD, UK; EN)