title: Stereoselective 1,2-additions of alpha-alkoxymethyllithiums to aldehydes.
abstract: [reaction: see text]. A chiral derivative of tributylstannylmethanol, readily prepared from L-valine, undergoes Sn-Li exchange to provide an alpha-alkoxyorganolithium that adds to aldehydes with up to 91:9 dr. The diastereoselectivity depends on the solvent and alkyllithium used for transmetalation. Treatment of adducts with acid allowed recovery of the chiral auxiliary and diol with complete stereochemical integrity.
authors.affiliation: Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry (GWC)(2), Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L3G1.
authors.forename: R P
authors.initials: RP
authors.lastname: Smyj
authors.forename: J M
authors.initials: JM
authors.lastname: Chong