Enantioselective synthesis of 4-amino-3-hydroxy-2,4-(disubstitut

Details Enantioselective synthesis of 4-amino-3-hydroxy-2,4-(disubstitut Enantioselective synthesis of 4-amino-3-hydroxy-2,4-(disubstitut

1983-01-03

1984-12-11

Shippen, Michael L.

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

Organic compounds

Carboxylic acids and salts thereof

560160, 560170, 548215, C07C10130

Patent

active

044879636

ABSTRACT:
4-Amino-3-hydroxy-2,4-(disubstituted)pentanoic acids of the formula: ##STR1## useful as intermediates in preparing antibacterial compounds, are synthesized enantiospecifically by acylation of a chiral enolate with an optically active acylating agent. The resulting product is reduced stereospecifically to afford a protected form of the desired product, which contains three adjacent asymmetric centers of known configuration. The synthesis may be illustrated as follows: ##STR2##

REFERENCES:
McOmie, "Protective Groups in Organic Chemistry," pp. 43, 72, 73 and 83-93 (1973).
Roberts, "Basic Principles of Organic Chemistry," pp. 287-291 and 301-304 (1964).
Evans et al., J. Am. Chem. Soc., (1981) 103, 2127.
J. Am. Chem. Soc., (1982) 104, 1737.
Takita et al., Tetrahedron Letters (1982) 23, 521.
Narita et al., Tetrahedron Letters (1982) 23,525.
J. Org. Chem., (1981) 46, 1232.
J. Amer. Chem. Soc., (1980) 102, 1452.
J. Antibiotics (1974) 27,356.

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