Process for intermediates to 1-carbapenems and 1-carbacephems

Details Process for intermediates to 1-carbapenems and 1-carbacephems Process for intermediates to 1-carbapenems and 1-carbacephems

1985-09-25

1988-05-17

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548188, 548110, C07D31726

Patent

active

047452013

ABSTRACT:
A stereoselective process for chiral intermediates to 1-carbapenum and 1-carbacephalosporins is provided comprising the use of an N-acyl-(4R)-substituted-1,3-thiazolidine-2-thione as a chiral auxiliary in boron enolate mediated aldol condensation with a protected-.beta.-keto ester aldehyde. E.g., benzyl 3,3-(ethylenedioxy)-4-formylbutyrate is condensed with the boron enolate formed with n-butyryl (4R)-methoxycarbonyl-1,3-thiazolidine-2-thione to provide benzyl 3,3-ethylenedioxy-(5R)-hydroxy-6-[(4R)-methoxycarbonyl-1,3-thiazolidine-2- thione-3-ylcarbonyl]octanoate. Displacement of the thiazolidine-2-thione chiral auxiliary moiety with an O-alkyl, O-acyl or O-aralkyl hydroxyamine provides the corresponding chiral intermediate as the hydroxamate.

REFERENCES:
Evans, D. A., et al., "Enantioselective Aldol Condensation. Erythro-Selective Chiral Aldol Condensation via Boron Enolates", J. Am. Chem. Soc., 1981, 103, 2127.
Wentrup, C., et al., "A Stereocontrolled Synthesis of (+)-Thienamycin", J. Am. Chem. Soc., 1980, 102, 6161-6163.
Salzmann, T. N., et al., "Total Synthesis of (-)-Homothienamycin", Tetrahedron Letters, vol. 21, pp. 1193-1196, 1980.
Soai, K., et al., "Synthesis of 1,3-Thizolidine-2-thione and (4R)-Methoxycarboxyl-1,3-thiazolidine-2-thione . . . ", Heterocycles, vol. 22, No. 12, 1984, 2827.
Nagao, Y., et al., Tetrahedron Letters, vol. 23, No. 2, pp. 201-204, 1984.
Jung, M., et al., Tetrahedron Letters, vol. 26, No. 8, pp. 977-980, 1985.

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