Tandem Wittig rearrangement/aldol reactions for the synthesis of glycolate aldols.
A new tandem Wittig Rearrangement/aldol reaction of O-benzyl or O-allyl glycolate esters is described. This reaction generates two carbon-carbon bonds and two contiguous stereocenters in a single step from simple starting materials. The [1,2]-Wittig rearrangement proceeds under very mild reaction conditions that do not require the use of a strong base, and the 1,2-diol products are obtained in good yield with excellent diastereoselectivity (>20:1).
Bertrand
Myra Beaudoin
MB
Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.
Wolfe
John P
JP
D000447:Aldehydes / Q000138:chemical synthesis*; D006016:Glycolates / Q000737:chemistry*
D000447:Aldehydes; D006016:Glycolates; C031149:glycolic acid; C116609:3-hydroxybutanal