Enantiopure α-Allyl-α-Amino Acids by Pd-Catalyzed Allylation of a Camphorsultam Modified Glycine Equivalent

Abstract

All articles of this category Palladium-catalyzed allylation of the chirally modified glycine equivalent N -(diphenylmethyleneaminoacetyl)camphorsultam 2 with a number of differently substituted allyl esters gave the corresponding protected α-allyl-α-amino acids 7/8 in 19-79% yield with 67 - >90% diasteromeric excess. Deprotection by consecutive treatment with 0.5 N HCl and 0.25 N LiOH leads to enantiopure α-amino acids, as exemplified by 2-amino-4-cyclopropylidenebutyric acid 4 . α-Allyl-α-amino acids - O’Donnell glycine equivalent - chirally modified - Palladium - π-Allyl intermediates