RESUMO
The use of lithio tris(methylthio)methane as a hydroxy/thio/amino carbonyl anion equivalent in the synthesis of α-amino acids is reported. Addition of the reagent to nonracemic sulfinimines furnished the α-sulfinamido trithioformates in excellent diastereoselectivity. Unmasking the trithioformates to diverse functionalities, such as α-amino acid thioesters, esters, anilides, amides, and di/tri peptides, without epimerization of chiral centers was accomplished.
Assuntos
Amidas , Ésteres , Amidas/química , Ésteres/química , Metano , Peptídeos , Compostos de Enxofre , Aminoácidos , Ânions , EstereoisomerismoRESUMO
Reaction of ω-halo-substituted nonracemic ß-sulfinamido ketones with NaH afforded the ß-amino cyclohexyl ketones in excellent yields and diastereoselectivity, via an intramolecular C-alkylation, α to the carbonyl group. The reaction was found to be general and can be applied for the synthesis of different cyclohexyl amino ketones and tetrahydropyrans possessing amine and acyl substitutions.