Diastereoselective Grignard Additions to O-Protected Polyhydroxylated Ketones: A Reaction Controlled by Groundstate Conformation?

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3938-3943

  Mulzer, Johann ^a   Pietschmann, Catarina ^a   Buschmann, Jürgen ^b   Luger, Peter ^b  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042228160     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961542v     Document Type: Article

References (16)

1. Reviews: (a) Devant, R. M.; Radunz, H.-E. Stereoselective Synthesis. In Houben-Weyl. Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds., Thieme: Stuttgart, 1995. Vol. E21b pp 1151-1334. (b) Huryn, D. M, In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 49-75.
2. Reviews: (a) Devant, R. M.; Radunz, H.-E. Stereoselective Synthesis. In Houben-Weyl. Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds., Thieme: Stuttgart, 1995. Vol. E21b pp 1151-1334. (b) Huryn, D. M, In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 49-75.
3. See also (c) Giuliano, R. M.; Villani, F. J., Jr. J. Org. Chem. 1995, 60, 202-211.
4. (a) Cram, D. J.; Abd Elhafez, F. A. J. Am. Chem. Soc. 1952, 74, 5828.
5. (b) Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204.
6. Anh, N. T. Top. Curr. Chem. 1980, 88, 145.
7. Reetz, M. T. Angew. Chem. 1984, 96, 542-555. Angew. Chem., Int. Ed. Engl. 1984, 23, 546.
8. Reetz, M. T. Angew. Chem. 1984, 96, 542-555. Angew. Chem., Int. Ed. Engl. 1984, 23, 546.
9. Lida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 3769-3771.
10. Fischer, J. C.; Horton, D.; W. Wecherle, W. Carbohydr. Res. 1977, 59, 459.
11. Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322-4343.
12. Nagano, H.; Ohno, M.; Miyamae, Y.; Kuno, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2814-2820.
13. Coxon, J. M.; Houk, K. N.; Luibrand, R. T. J. Org. Chem. 1995, 60, 418-427.
14. Schmidt, C. R.; Bryant, J. D.; Dowlatzedah, M.; Phillips, J. L.; Prather, D. E.; Schantz, R. D.; Sear, N. L.; Vianco, C. S. J. Org. Chem. 1991, 56, 4056-4058.
15. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991.
16. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.