Two step synthesis of D- and L- .alpha.-amino acids and D- and L- .alpha.-amino-aldehydes
 D- and L-.alpha.-amino acids and D- and L-.alpha.-amino aldehydes are synthesized from olefin substrates in two steps. The first step is a catalyzed asymmetric aminohydroxylation addition reaction to the olefin substrate. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantioselectively. Divalent ligands are preferred over monovalent ligands because of their enhance regio- and enantio-selectivity. As an oxidant nitrogen source for the addition reaction, either a carbamate or sulfonamide may be employed. If carbamate is employed as an oxidant nitrogen source, the resultant .beta.-hydroxycarbamate is deprotected to yield the corresponding .beta.-hydroxyamine. If sulfonamide is employed as an oxidant nitrogen source, the resultant .beta.-hydroxysulfonamide is deprotected to yield the corresponding .beta.-hydroxyamine. The resultant .beta.-hydroxyamine is then selectively oxidized in a second synthetic step to produce the desired D- and L-.alpha.-amino acid or D- and L-.alpha.-amino aldehyde. 
The Scripps Research Institute
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Guigen K. Barry
Li Sharpless