Process for synthesis of chiral cis-and trans-3-amino-4 substitu

Details Process for synthesis of chiral cis-and trans-3-amino-4 substitu Process for synthesis of chiral cis-and trans-3-amino-4 substitu

1996-12-12

1997-09-16

McKane, Joseph K.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

548230, C07D41306

Patent

active

056681640

ABSTRACT:
Process for preparation of chiral cis-3,4-substituted pyrrolidine compounds having the formulas: ##STR1## and chiral 3,4-trans-substituted pyrrolidine compounds having the formulas: ##STR2## with the assistance of a streochemically directing chiral oxazolidinone moiety having the formula: ##STR3## wherein P, R and R.sup.1 are specifically defined, by sequential reaction of the compound or subsequent intermediates with an a,b-unsaturated add chloride, reaction with N-benzyl-N-(methoxymethyl)trimethyl-silylmethylamine and separating isomers by chromatography, hydrolytic removal of the oxazolidinone moiety, reaction with diphenylphosphoryl azide and triethylamine, and debenzylating; and novel intermediates of the process.

REFERENCES:
Williams, R. M., et al., "Asymmetric Synthesis of S-(-)-Cucurbitine", Tetrahedron Letters, vol. 33, No. 45, pp. 6735-6758, 1992.
Rispens, M. T., et al., "Asymmetric 1,3-Dipolar Cycloadditions to 5-(R)-Menthyloxy-2(5H)-Furanone", Tetrahydron: Asymmetry, vol. 5, No. 4, pp. 607-624, 1994.
Fray, A. H., et al., "Diastereoselective Azomethine Ylide Cycloadditions to Unsaturated, Chiral Bicyclic Lactams", Tetrahydron Letters, vol. 33, No. 25, pp. 3575-3578, 1992.
Wee, A. G. H., J. Chem. Soc., Perkin Trans. 1, pp. 1363-1364, 1989.
CA 124: 8797 Improved chiral auxillaries . . . and their use. Davies et al. Jul. 1995.

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