Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1989-06-21
1992-05-12
Lee, Mary C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549 29, C07D32710
Patent
active
051129906
ABSTRACT:
A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various substituted products. The method is an efficient means for the synthesis of chiral building blocks from tartaric acid enantiomers in high yields using an overall two-stage, one-pot reaction procedure. The chiral compounds can be transformed by nucleophilic reactions into chiral building blocks useful for the synthesis of natural biologically active products, such as antibiotics and pheromones.
REFERENCES:
Chem. Abstracts vol. 108, abst. No. 37493n (abst. of Stampa, ES 533,294, Sep. 1, 1986).
D. S. Breslow and H. Skolnik, The Chemistry of Heterocyclic Compounds-Multi-Sulphur and Sulphur and Oxygen 5- and 6-Membered Heterocycles, 1966, Part 1, p. 1 and Part 2, pp. 633, 639.
G. Lowe and S. J. Salamone, J. Chem. Soc., Chem. Commun., 1392-1394 (1983).
D. Seebach, In: Modern Synthetic Methods 1980, 1:115-171 (1980).
S. Saito et al., Tetrahedron Letters, 27(43):5249-5252 (1986).
T. G. Hansson and J. O. Kihlberg, J. Org. Chem., 51:4490-4492 (1986).
E. Hungerbuhler et al., Angew. Chem. Int. (Engl. Ed.) 18(12):958-960 (1979).
M. J. Miller et al., J. Org. Chem., 47:4928-4933 (1982).
J. S. Bajwa and M. J. Miller, J. Org. Chem., 48:1114-1116 (1983).
P. Schnurrenberger et al., Liebigs Ann. Chem., 733-744 (1987).
S. Saito et al., Tetrahedron Letters, 26(43):5309-5312 (1985).
K. Mori and H. Iwasawa, Tetrahedron, 36:87-90 (1980).
T. G. Hansson and J. O. Kihlberg, J. Org. Chem., 51:4490-4492 (1986).
S. J. Brandes and J. A. Katzenellenbogen, Molecular Pharmacology, 32:391-403 (1987).
Gao et al., JACS, 110:7538-7539 (1988).
Gao Yun
Sharpless K. Barry
Haley Jacqueline
Lee Mary C.
Massachusetts Institute of Technology
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