74262-70-7Relevant academic research and scientific papers
ALDOL ADDITIONS to α- AND β-ALKOXY ALDEHYDES : THE EFFECT OF CHELATION ON SIMPLE DIASTEREOSELECTIVITY
Reetz, M. T.,Kesseler, K.,Jung, A.
, p. 4327 - 4336 (2007/10/02)
The TiCl4 or SnCl4 mediated reaction of enol silanes with chiral α- or β-alkoxy aldehydes constitutes the only presently known, general way to perform aldol additions with chelation-control (asymmetric induction >90percent).If the enol silane is prochiral
Acyclic Stereoselection. 9. Stereochemistry of the Addition of Lithium Enolates to α-Alkoxy Aldehydes
Heathcock, Clayton H.,Young, Steven D.,Hagen, James P.,Pirrung, Michael C.,White, Charles T.,VanDerveer, Don
, p. 3846 - 3856 (2007/10/02)
The stereochemistry of addition of lithium enolates derived from esters and ketones to the α-alkoxy aldehydes 1-5 has been investigated.In all cases, the predominant product is that predicted by application of Felkin's model for asymmetric induction and by assuming the alkoxy group to be the "large" group.The Cram cyclic model for asymmetric induction is not followed.Stereostructures have been assigned by a combination of conversion to products of known stereostructure, 13C and 1H NMR correlations, and single-crystal X-ray analysis.
