Two step synthesis of D- and L- .alpha.-amino acids and D- and L

Details Two step synthesis of D- and L- .alpha.-amino acids and D- and L Two step synthesis of D- and L- .alpha.-amino acids and D- and L

1996-05-22

1999-11-30

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

562553, C07C22904

Patent

active

059945834

ABSTRACT:
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.

REFERENCES:
patent: 4871855 (1989-10-01), Marko
CA:8941984 Abs Gazz Chim Ital 107 (9-10),Paiaro, pp. 467-472, 1977.
CA:118169412, ab s of WO9220677, Nov. 1992.
CA:122:9606, Sharpless, Tetrahedron Asymmetry 5 (8), pp. 1473-1476, 1994.
CA121;179066, Tetrahedron lettm 35(29) Sharpless, pp. 5129-5132, 1994.
CA:76:45490, Marken, Dissertation Univ Microfilms Ann Arbor Mich Order NO 41-21, 176, 1972
CA:80:59624, Ohgo, Chem lett. (1) pp. 33-36, 1974.
CA:124:29604, abs of WO9517386, Jun. 1995.
CA:78:123587, ABS of J Amer Chem, 95 (5), Noyori, pp. 1674-1676, 1973.
CA:110:172656 abst of "Convenient synthesis of vicinal diamines", Jones, J Org Chem 54(8) pp. 1940-1943, 1989.
CA:109:230851 abst of "Palladium catalyzed intramolecular aminocarbonylation" Tamaru, J Org Chem 53(24) pp. 5731-5741, 1988.

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