TANDEM ALDOLIZATION / LACTONIZATION / DYOTROPIC REARRANGEMENT OF α-AMINO-ALDEHYDES

Article abstract of DOI:10.1016/S0040-4039(01)80583-9

N,N-dibenzyl-protected α-amino-aldehydes 1 undergo non-chelation-controlled aldol additions of 1-phenoxy-1-trimethylsiloxyethylene 2 followed by β-lactone formation and dyotropic rearrangement, all three reactions being catalyzed by MgCl2.The products, 4-substituted 3-amino-χ-lactones 3, are stereochemically pure (de and ee > 99percent).