Enantiocontrol in tandem carbonyl ylide formation and intermolecular 1,3-dipolar cycloaddition of α-diazo ketones mediated by chiral dirhodium(II) carboxylate catalyst [20]

Journal of the American Chemical Society

Volumn 121, Issue 6, 1999, Pages 1417-1418

  Kitagaki, Shinji ^b   Anada, Masahiro ^b   Kataoka, Osamu ^a,b   Matsuno, Kentaro ^b   Umeda, Chisato ^b   Watanabe, Nobuhide ^b   Hashimoto, Shun Ichi ^b  

^a KANAZAWA UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPPER; KETONE; LIGAND; RHODIUM DERIVATIVE;

CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; LETTER; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033576992     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983748e     Document Type: Letter

References (36)

1. (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
2. (b) Padwa, A. Chem. Commun. 1998, 1417.
3. (a) Doyle, M. P. Chem. Rev. 1986, 86, 919.
4. (b) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
5. (c) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
6. (a) Doyle, M. P. Aldrichimica Acta 1996, 29, 3.
7. (b) Hashimoto, S.-I.; Watanabe, N.; Anada, M.; Ikegami, S. J. Synth. Org. Chem., Jpn. 1996, 54, 988.
8. (c) Davies, H. M. L. Aldrichimica Acta 1997, 30, 107.
9. (d) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
10. (e) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley-Interscience: New York, 1998.
11. For examples of enantioselective rearrangement via oxonium, sulfonium, or selenonium ylides generated by catalytic diazo decomposition: (a) McCarthy, N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983.
12. (b) Nishibayashi, Y.; Ohe, K.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 1245.
13. (c) Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1997, 38, 3435.
14. (d) Pierson, N.; Fernández-García, C.; McKervey, M. A. Tetrahedron Lett. 1997, 38, 4705.
15. (e) Clark, J. S.; Fretwell, M.; Whitlock, G. A.; Burns, C. J.; Fox, D. N. A. Tetrahedron Lett. 1998, 39, 97. The asymmetric induction observed here has been attributed to the creation of chiral, nonracemic free ylides after dissociation of the catalyst rather than involvement of the catalyst in the product-forming step.
16. Following the early suggestion by Roskamp and Johnson, Doyle and co-workers have recently demonstrated that a metal-associated ylide is the primary product-forming intermediate in enantioselective intermolecular ylide generation/[2,3]-sigmatropic rearrangement with allyl iodide whose free ylide is achiral: (a) Roskamp, E. J.; Johnson, C. R. J. Am. Chem. Soc. 1986, 108, 6062.
17. (b) Doyle, M. P.; Forbes, D. C.; Vasbinder, M. M.; Peterson, C. S. J. Am. Chem. Soc. 1998, 120, 7653.
18. (a) Padwa, A.; Austin, D. J.; Hornbuckle, S. F.; Price, A. T. Tetrahedron Lett. 1992, 33, 6427.
19. (b) Padwa, A.; Austin, D. J.; Hornbuckle, S. F. J. Org. Chem. 1996, 61, 63.
20. For a more recent suggestion, see: (a) Doyle, M. P.; Forbes, D. C.; Protopopova, M. N.; Stanley, S. A.; Vasbinder, M. M.; Xavier, K. R. J. Org. Chem. 1997, 62, 7210.
21. (b) Doyle, M. P.; Forbes, D. C.; Xavier, K. R. Russ. Chem. Bull. 1998, 47, 932.
22. Hodgson, D. M.; Stupple, P. A.; Johnstone, C. Tetrahedron Lett. 1997, 38, 6471.
23. 4 afforded 1,3-dipolar cycloadduct in high exo-selectivity, albeit in low enantioselectivities (endo: 20% ee: exo: 5% ee): Suga, H.; Ishida, H.; Ibata, T. Tetrahedron Lett. 1998, 39, 3165.
24. 4, to form the all-cis 1,3-dioxolane as the major product in 28% ee. See ref 3d.
25. Enantioselective aziridine formation with benzylideneaniline and ethyl diazoacetate catalyzed by Cu(I)L* has been reported, where a free ylide intermediate is improbable: Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. Engl. 1995, 34, 676.
26. Padwa, A.; Fryxell, G. E.; Zhi, L. J. Am. Chem. Soc. 1990, 112, 3100.
27. Hashimoto, S.-I.; Watanabe, N.; Sato, T.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1993, 34, 5109.
28. Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450.
29. Substantial amounts (ca. 10-15%) of the cycloheptatriene derivatives were formed by way of the bimolecular addition of the rhodium(II) carbene carbon onto the benzene ring.
30. (a) Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S.-I. Synlett 1996, 85.
31. (b) Anada, M.; Hashimoto, S.-I. Tetrahedron Lett. 1998, 39, 79.
32. (c) Anada, M.; Watanabe, N.; Hashimoto, S.-I. Chem. Commun. 1998, 1517.
33. 4 were 6% and 2%, respectively.
34. Kitagaki, S.; Matsuda, H.; Watanabe, N.; Hashimoto, S.-I. Synlett 1997, 1171.
35. The syntheses of the new catalysts are described in the Supporting Information.
36. Padwa, A.; Chinn, R. L.; Hornbuckle, S. F.; Zhang, Z. J. J. Org. Chem. 1991, 56, 3271.