A new type of complex reagent, R4Pb / TiCl4

Article abstract of DOI:10.1016/0040-4020(92)80009-5

Tetraalkllleads (R₄Pb) reacted quite smoothly with aldehydes R'CHO in the presence of TiCl₄ to produce the corresponding alcohols (RCHOHR′) in high to good yields. The reagent system, R₄Pb/ TiCl₄, exhibited high chemoselectivity; only aldehydes underwent the alkylation in the presence of ketones. Further, the new reagent exhibited high 1,2- and 1,3-asymmetric induction. The transfer order of alkyl groups in the reaction of aldehydes with mixed tetraalkylleads/TiCl₄ was determined; Me>Et.i-Pr?n-Bu.