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Diastereoselective Synthesis of Unnatural Amino Acids by Alkylation of α- tert-Butanesulfinamide Auxiliary-Bound Enolates.

A new chiral auxiliary for the diastereoselective alkylation of amino ester enolates that takes advantage of chiral information stored on the enolate side of the amino ester substrate has been developed. Chiral α-sulfinamido esters were alkylated under basic conditions in good yields (up to 90%) and good to high diastereoselectivities (generally >6:1) to provide unnatural mono- and α,α-disubstituted amino acid derivatives. This auxiliary allowed for the ready conversion of ester functionality without the need for esoteric reagents. Furthermore, the auxiliary is easily removed to provide enantiopure amino acids. Computational studies revealed that a chelated transition state governs electrophile addition from the convex face of a transient bicyclic intermediate. This method allows ready access to enantioenriched natural and unnatural amino acids.