Hydroxyl-directed reductive cleavage of 3-oxetanols as an entry to diastereomerically pure 1,2-diols

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3900-3901

  Bach, Thorsten ^a   Kather, Kristian ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000832711     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952235c     Document Type: Article

References (26)

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2. (a) Seebaeh, D. Angew. Chem. 1979, 91, 259; Angew. Chem., Int. Ed. Engl. 1979, 18, 239.
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4. For recent reviews, see: (a) Mattay, J.; Conrads, R.; Hoffmann, R. In Methoden der Organischen Chemie (Houben-Weyl); 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995, Vol. E 21c; p 3133. (b) Porco, J. A.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B., Ed.; Pergamon Press: Oxford, 1991; Vol. 5; p 151. (c) Carless, H. A. J. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: New York, 1984; p 425. (d) Jones, G. In Organic Photochemistry; Padwa, A., Ed.; Dekker: New York 1981; Vol. 5; p 1.
5. For recent reviews, see: (a) Mattay, J.; Conrads, R.; Hoffmann, R. In Methoden der Organischen Chemie (Houben-Weyl); 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995, Vol. E 21c; p 3133. (b) Porco, J. A.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B., Ed.; Pergamon Press: Oxford, 1991; Vol. 5; p 151. (c) Carless, H. A. J. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: New York, 1984; p 425. (d) Jones, G. In Organic Photochemistry; Padwa, A., Ed.; Dekker: New York 1981; Vol. 5; p 1.
6. For recent reviews, see: (a) Mattay, J.; Conrads, R.; Hoffmann, R. In Methoden der Organischen Chemie (Houben-Weyl); 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995, Vol. E 21c; p 3133. (b) Porco, J. A.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B., Ed.; Pergamon Press: Oxford, 1991; Vol. 5; p 151. (c) Carless, H. A. J. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: New York, 1984; p 425. (d) Jones, G. In Organic Photochemistry; Padwa, A., Ed.; Dekker: New York 1981; Vol. 5; p 1.
7. For recent reviews, see: (a) Mattay, J.; Conrads, R.; Hoffmann, R. In Methoden der Organischen Chemie (Houben-Weyl); 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995, Vol. E 21c; p 3133. (b) Porco, J. A.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B., Ed.; Pergamon Press: Oxford, 1991; Vol. 5; p 151. (c) Carless, H. A. J. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: New York, 1984; p 425. (d) Jones, G. In Organic Photochemistry; Padwa, A., Ed.; Dekker: New York 1981; Vol. 5; p 1.
8. (a) Bach, T. Tetrahedron Lett. 1991, 32, 7037.
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11. 4 and related reagents in oxetane ring opening, see: (a) Searles, S., Jr.; Pollart, K. A.; Lutz, E. F. J. Am. Chem. Soc. 1957, 79, 948. (b) Seyden-Penne, J.; Schaal, C. Bull. Soc. Chim. Fr. 1969, 3653. (c) Ruotsalainen, H.; Palosaari, V.; Olavi, I. P. Suom. Kemistil. B 1972, 45, 40.
12. 4 and related reagents in oxetane ring opening, see: (a) Searles, S., Jr.; Pollart, K. A.; Lutz, E. F. J. Am. Chem. Soc. 1957, 79, 948. (b) Seyden-Penne, J.; Schaal, C. Bull. Soc. Chim. Fr. 1969, 3653. (c) Ruotsalainen, H.; Palosaari, V.; Olavi, I. P. Suom. Kemistil. B 1972, 45, 40.
13. 4 and related reagents in oxetane ring opening, see: (a) Searles, S., Jr.; Pollart, K. A.; Lutz, E. F. J. Am. Chem. Soc. 1957, 79, 948. (b) Seyden-Penne, J.; Schaal, C. Bull. Soc. Chim. Fr. 1969, 3653. (c) Ruotsalainen, H.; Palosaari, V.; Olavi, I. P. Suom. Kemistil. B 1972, 45, 40.
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17. Bach, T.; Kather, K. Tetrahedron 1994, 50, 12319. For related migrations on 3-oxetanols, see: Kagan, J.; Przybytek, J. T. Tetrahedron 1973, 29, 1163.
18. Bach, T.; Kather, K. Tetrahedron 1994, 50, 12319. For related migrations on 3-oxetanols, see: Kagan, J.; Przybytek, J. T. Tetrahedron 1973, 29, 1163.
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21. (a) For the stereoselective addition of allylic metal compounds to form this type of 1,2-diols, see: Hoffmann, R. W.; Metternich, R. Liebigs Ann. Chem. 1986, 2390.
22. (b) For aldol reactions, see: Montgomery, S. H.; Pirrung, M. C.; Heathcock, C. H. Carbohydr. Res. 1990, 202, 13.
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