An Asymmetric Synthesis of Optically Pure α,α-Disubstituted Amino Aldehydes, α,α-Disubstituted Amino Acids, and Sterically Demanding Dipeptides

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Abstract

Optically pure α-methyl-α-alkyl amino aldehydes were efficiently synthesized from the cyclohexylimine of propanal bearing an α-4(R),5(S)-diphenyl-2-oxazolidinone by asymmetric alkylation of the imine anion. α-Methylphenylalanine and α-methylleucine were synthesized in two steps from the corresponding amino aldehydes. Utilizing an oxaziridine rearrangement, amino aldehydes were converted to dipeptides in which both the amino and carboxy components were α,α-disubstituted.

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