Process for stereochemically inverting a hydroxy function of an

Details Process for stereochemically inverting a hydroxy function of an Process for stereochemically inverting a hydroxy function of an

1988-09-16

1990-03-27

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20700

Patent

active

049122304

ABSTRACT:
A process is provided for inverting a hydroxy function of a L-trans-hydroxy proline derivative to the corresponding L-cis-hydroxy proline sulfonate by a Modified Mitsunobu reaction process.

REFERENCES:
Noller, Textbook of Organic Chemistry, W. B. Saunders Co., Philadelphia, 1966, pp. 173, 226.
D. L. Hughes, R. A. Reamer, J. J. Bergan, and E. J. J. Grabowski, in Journal of the American Chemical Society (1988), vol. 110, No. 19, pp. 6487-6491.
Oyo Mitsunobu, in Synthesis (1981), pp. 1-28, "The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products".
Amos B. Smith, III et al., in Tetrahedron Letters (1986), vol. 27, No. 48, pp. 5813-5816, "An Efficient Synthesis of Glycosyl Esters Exploiting the Mitsunobu Reaction".
Igor Galynker et al., in Tetrahedron Letters (1982), vol. 23, No. 43, pp. 4461-4464, "A Simple Method for Tosylation with Inversion".
J. R. Falck et al., in Tetrahedron Letters (1984), vol. 25, No. 23, pp. 2443-2446, "Enantiospecific Synthesis of Methyl 11,12- and 14,15-Epoxyeicosatrienoate".
Patrick Rollin, in Synthetic Communications (1986), 16(6), 611-616, "Nucleophilic Inversions of a Chiral Alcohol Medicated by Zinc Salts".

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