Highly enantioselective oxonium ylide formation and stevens rearrangement catalyzed by chiral Dirhodium(II) carboxamidates

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4367-4370

  Doyle, Michael P ^a   Ene, Doina G ^a   Forbes, David C ^a   Tedrow, Jason S ^a  

^a TRINITY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE;

ARTICLE; CATALYSIS; CONFORMATION; DECOMPOSITION; ENANTIOMER; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030913338     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00930-1     Document Type: Article

References (14)

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2. Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S. Ed.; Pergamon Press, New York, 1995; Vol. 12, Chapter 5.2.
3. Doyle, M. P.; Bagheri, V.; Claxton, E. E. J. Chem. Soc., Chem. Commun. 1990, 46.
4. West, F. G.; Naudu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892.
5. Clark, J. S.; Dossetter, A. G.; Whittingham, W. G. Tetrahedron Lett. 1996, 37, 5605.
6. Brogan, J. B.; Bauer, C. B.; Rogers, R. D.; Zercher, C. K. Tetrahedron Lett. 1996, 37, 5053.
7. McCarthy, N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983.
8. (a) Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron 1996, 52, 3905.
9. (b) Ito, K.; Yoshitake, M.; Katsuki, T. Heterocycles 1996, 42, 305.
10. This derivative is not available through direct reaction of 2-deoxyribonolactone with acetone: Han, S.-Y.; Joullié, M. M.; Petasis, N. A.; Bigorra, J.; Corbera, J.; Font, J.; Ortuno, R. M. Tetrahedron 1993, 49, 349.
11. All new products were identified from their characteristic spectra, and elemental analyses confirmed their composition. Enantiomeric excesses were obtained from GC analyses on Chiraldex columns with baseline resolution; for example, both 5 and 6 were analyzed on a 30-m Chiraldex B-PH column with enantiomer separations of 5 and 8 min, respectively.
12. Doyle, M. P.; Winchester, W. R.; Hoorn, J. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968.
13. Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. I.; Miertschin, C. S.; Winchester, W. R. Rec. Trav. Chim. Pays-Bas 1995, 114, 163.
14. Doyle, M. P.; Zhou, Q.-L.; Raab, C. E.; Roos, G. H. P.; Simonsen, S. H.; Lynch, V. Inorg. Chem. 1996, 118, 8837.