Diastereodifferentiation in intramolecular cyclopropanations of chiral secondary allylic diazoacetates

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 2929-2932

  Martin, Stephen F ^a   Hillier, Michael C ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER;

ARTICLE; CATALYSIS; CATALYST; CONFORMATIONAL TRANSITION; MOLECULAR INTERACTION; STEREOISOMERISM; SYNTHESIS;

EID: 0032493016     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00501-2     Document Type: Article

References (20)

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2. (b) Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Baker, W. R.; Condon, S. L.; DeLara, E.; Rosenberg, S. H.; Spina, K. P.; Stein, H. H.; Cohen, J.; Kleinen, H. D. J. Med. Chem. 1992, 35, 1710-1721.
3. (c) Baker, W. R.; Jae, H.-S.; Martin, S. F.; Condon, S. L.; Stein, H. H.; Cohen, J.; Kleinen, H. D. Bioorg. Med. Chem. Lett. 1992, 2, 1405.
4. (d) Martin, S. F.; Oalmann, C. J.; Liras, S. Tetrahedron 1993, 49, 3521.
5. 2. (a) Doyle, M. P.; Pieters, R. J.; Martin, S. F.; Austin, R. E.; Oalmann, C. J.; Müller, P. J. Am. Chem. Soc. 1991, 113, 1423-1424.
6. (b) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763-5775
7. 3. (a) Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494.
8. (b) Doyle, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Ruppar, D. A.; Martin, S. F.; Spaller, M. R.; Liras, S. J. Am. Chem. Soc. 1995, 117, 11021-11022.
9. 4. (a) Yadav, J. S.; Chander, M. C.; Joshi, V. B. Tetrahedron Lett. 1988, 29, 2737-2740.
10. (b) Yadav, J. S.; Chander, M. C.; Rao, C. S. Tetrahedron Lett. 1989, 30, 5455-5458.
11. (c) Yadav, J. S.; Vidyanand, D.; Rajagopal, D. Tetrahedron Lett. 1993, 34, 1191-1194.
12. 1H NMR. Analytical samples of all new compounds were obtained by distillation, recrystallization, preparative HPLC or flash chromatography and gave satisfactory identification by high resolution mass spectrometry.
13. 6. Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017-3020.
14. 7. Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403-6406.
15. 8. (a) Marvell, E. N.; Li, T. Synthesis 1973, 457-468.
16. (b) Denmark, S. E.; Jones, T. K. J. Org. Chem. 1982, 4595-4597.
17. 9. Corey, E. J.; Myers, A. G. Tetrahedron Lett. 1984, 25, 3559-3562.
18. 2 (90 mL) over 18-24 h.
19. 11. The structure of 6b was established by X-ray crystallography. The coordinates have been deposited in the Cambridge Crystallographic Data Center.
20. 12. Doyle, M. P.; Dyatkin, A. B. J. Org. Chem. 1995, 60, 3035-3038.