Chemo- and stereoselective dirhodium(II)-catalyzed C-H insertion reaction of 5,6-dioxygenated 2-diazo-3-oxohexanoates: Synthesis of an optically active highly functionalized cyclopentane

Tetrahedron

Volumn 55, Issue 24, 1999, Pages 7461-7470

  Yakura, Takayuki ^a   Ueki, Akiharu ^a   Kitamura, Tsuyoshi ^a   Tanaka, Kenji ^a   Nameki, Masatake ^a   Ikeda, Masazumi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Carbenes and carbenoids; Cyclopentanes; Insertion reactions; Rhodium and compounds

Indexed keywords

CARBONYL DERIVATIVE; CYCLOPENTANE DERIVATIVE; RHODIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033546338     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00369-5     Document Type: Article

References (48)

1. For reviews, see: Doyle, M. P. Acc. Chem. Res. 1986, 19, 348;
2. Doyle, M. P. Chem. Rev. 1986, 86, 919;
3. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765;
4. Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385;
5. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091;
6. Padwa, A.; Austin, D. J. Angew. Chem. Int. Ed. Engl. 1994, 35, 1797;
7. Doyle, M. P. Aldrichimica Acta 1996, 29, 3;
8. Hashimoto, S.; Watanabe, N.; Anada, M.; Ikegami, S. J. Synth. Org. Chem., Jpn. 1996, 54, 988;
9. Zaragoza, F. Tetrahedron 1997, 53, 3425;
10. Doyle, M. P.; McKervey, M. A. Chem. Commun. 1997, 983;
11. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911;
12. Sulikowski, G. A.; Cha, K. L.; Sulikowski, M. M. Tetrahedron: Asymmetry 1998, 9, 3145;
13. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; John Willey & Sons: New York, 1998.
14. (a) Yakura, T.; Yoshida, D.; Ueki, A.; Nakao, K.; Ikeda, M. Chem. Pharm. Bull. 1997, 45, 651.
15. (b) Yakura, T.; Yamada, S.; Kunimune, Y.; Ueki, A.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 3643.
16. Yakura, T.; Yamada, S.; Azuma, M.; Ueki, A.; Ikeda, M. Synthesis 1998, 973.
17. For a review, see: Martínez-Grau, A.; Marco-Contelles, J. Chem. Soc. Rev. 1998, 27, 155.
18. For recent syntheses of aminocyclopentitols, see: Boiron, A.; Zillig, P.; Faber, D.; Giese, B. J. Org. Chem. 1998, 63, 5877;
19. de Gracia, I. S.; Dietrich, H.; Bobo, S.; Chiara, J. L. J. Org. Chem. 1998, 63, 5883;
20. Ling, R.; Mariano, P. S. J. Org. Chem. 1998, 63, 6072. See also references cited therein.
21. For reviews, see: Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745;
22. Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571;
23. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611;
24. Crimmins, M. T. Tetrahedron 1998, 54, 9229.
25. A part of this work has appeared as a preliminary communication: Yakura, T.; Ueki, A.; Morioka, Y.; Kurata, T.; Tanaka, K.; Ikeda, M. Chem. Pharm. Bull. 1998, 46, 1182.
26. Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389.
27. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258.
28. Sugita, Y.; Sakaki, J.; Sato, M.; Kaneko, C. J. Chem. Soc., Perkin Trans. 1 1992, 2855.
29. When the reaction was carried out at room temperature, yields of 5 and 11 decreased.
30. 2 at room temperature gave a 1:1 mixture of 2,2-dimethyl-3,8-dioxabicyclo[3.2.1]octan-7-one (19) and the C-H insertion product 20 in 60% combined yield, see: Tester, R. W.; West, F. G. Tetrahedron Lett. 1998, 39, 4631.
31. Doyle and co-workers have recently described a similar oxonium ylide formation/1,2-shift of acetonide derivatives with chiral dirhodium reagents, see: Doyle, M. P.; Ene, D. G.; Forbes, D. C.; Tedrow, J. S. Tetrahedron Lett. 1997, 38, 4367.
32. For a review, see: Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
33. For the oxonium ylide formation reactions using dirhodium catalysts, see: Brogan, J. B.; Zercher, C. K. Tetrahedron Lett. 1998, 39, 1691;
34. Brogan, J. B.; Zercher, C. K.; Bauer, C. B.; Rogers, R. D. J. Org. Chem. 1997, 62, 3902;
35. Brogan, J. B.; Bauer, C. B.; Rogers, R. D.; Zercher, C. K. Tetrahedron Lett. 1996, 37, 5053. See also references cited therein.
36. 4 under the same conditions, followed by purification by silica gel column chromatography gave the corresponding cyclopentenones in lower yields (37-40%).
37. Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958;
38. Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547;
39. Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 6706.
40. Gorthey, L. A.; Vairamani, M.; Djerassi, C. J. Org. Chem. 1985, 50, 4173;
41. Nagao, Y.; Goto, M.; Ochiai, M.; Shiro, M. Chem. Lett. 1990, 1503;
42. Nagao, Y.; Goto, M. Heterocycles 1995, 41, 883;
43. Eliel, E. L.; Satici, H. J. Org. Chem. 1994, 59, 688.
44. Dauben, W. G.; Lewis, T. A. Synlett 1995, 857.
45. The authors have 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, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, UK.
46. Fan, H.-F. (1991). Structure analysis programs with intelligent control, Rigaku Corporation, Tokyo, Japan.
47. Cromer D. T.; Waber J. T. In International Tables for X-ray Crystallography; The Kynoch Press: Birmingham, 1974; Vol. 4, Table 2.2 A.
48. Crystal Structure Analysis Package, Molecular Structure Corporation (1985 and 1992).