Amplification of asymmetric induction in sequential reactions of bis-diazoacetates catalyzed by chiral dirhodium(II) carboxamidates

Organic Letters

Volumn 7, Issue 22, 2005, Pages 5035-5038

  Doyle, Michael P ^a   Wang, Yuanhua ^a   Ghorbani, Pejman ^a   Bappert, Erhard ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; DIAZONIUM COMPOUND; HETEROCYCLIC COMPOUND; ORGANOMETALLIC COMPOUND; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ACETATES; CATALYSIS; DIAZONIUM COMPOUNDS; HETEROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 27644451809     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0520121     Document Type: Article

References (25)

1. (a) Doyle, M. P. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000.
2. (b) Doyle, M. P. In Topics in Organometallic Chemistry; Dotz, K.-H., Ed.; Springer-Verlag GmbH: Berlin, Germany, 2004; Vol. 10, p 203.
3. (c) Doyle, M. P. In Modern Rhodium-Catalyzed Transformations; Evans, P. A., Ed.; Wiley-VCH: New York, 2005.
4. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998.
5. (a) Davies, H. M. L.; Antoulinakis, E. G. Org. React. 2001, 57, 1.
6. (b) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
7. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
8. (a) Davies, H. M. L.; Jin, Q. Org. Lett. 2005, 7, 2293.
9. (b) Davies, H. M. L.; Venkataramani, C. Org. Lett. 2001, 3, 1773.
10. Amplification of asymmetric induction and double stereodifferentiation are discussed in Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; Chapter 12.5.
11. Examples of the broad applications of double stereodifferentiation include: (a) Heathcock, C. H.; White, C. T. J. Am. Chem. Soc. 1979, 101, 7076.
12. (b) Starkmann, B. A.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 2002, 725.
13. (c) Togni, A.; Blumer, R. K.; Pregosin, P. S. Helv. Chim. Acta 2004, 74, 1533.
14. (a) Martin, S. F.; Spalier, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493.
15. (b) Doyle, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Ruppar, D. A.; Martin, S. F.; Spallar, M. R.; Liras, S. J. Am. Chem. Soc. 1995, 117, 11021.
16. Doyle, M. P.; Morgan, J. P.; Fettinger, J.; Colyer, J. T.; Timmons, D. J.; Carducci, M. J. Org. Chem. 2005, 70, 5291.
17. Taber, D. F.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686.
18. (a) Doyle, M. P.; Kalinin, A. V.; Ene, D. G. J. Am. Chem. Soc. 1996, 118, 8837.
19. (b) Doyle, M. P.; Tedrow, J. S.; Dyatkin, A. B.; Spaans, C. J.; Ene, D. G. J. Org. Chem. 1999, 64, 8907.
20. (c) Doyle, M. P.; Colyer, J. J. Mol. Catal. A 2003, 196.
21. (d) Doyle, M. P.; Yan, M.; Gau, H.-M; Blossey, E. C. Org. Lett. 2003, 5, 561.
22. Doyle, M. P.; Davies, S. B.; May, E. J. J. Org. Chem. 2001, 66, 8112.
23. Only products from intermolecular and intramolecular "carbene dimer" formation were observed from reactions of the bis-diazoacetate of cis-1,4-cyclohexanediol.
24. Crystallographic data for 2, 3, and 4 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 279653, 279654, 279655. See Supporting Information for X-ray crystal data.
25. 4.