Catalytic addition methods for the synthesis of functionalized diazoacetoacetates and application to the construction of highly substituted cyclobutanones

Organic Letters

Volumn 7, Issue 23, 2005, Pages 5171-5174

  Doyle, Michael P ^a   Kundu, Kousik ^a   Russell, Albert E ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CYCLOBUTANE DERIVATIVE; RHODIUM; SCANDIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ACETATES; CATALYSIS; CYCLIZATION; CYCLOBUTANES; MOLECULAR STRUCTURE; RHODIUM; SCANDIUM; STEREOISOMERISM;

EID: 28244496616     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052003s     Document Type: Article

References (40)

1. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; John Wiley & Sons: New York, 1998.
2. Reviews: (a) Merlic, C. A.; Zechman, A. L. Synthesis 2003, 1137-1156.
3. (b) Davies, H. M. L.; Antoulinakis, E. G. Org. React. 2001, 57, 1-326.
4. (c) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50-61.
5. (d) Doyle, M. P. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; John Wiley & Sons: New York, 2000.
6. (e) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911-935.
7. (f) Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Adv. Heterocycl. Chem. 1996, 65, 93-233.
8. (g) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797-1815.
9. (a) Padwa, A.; Austin, D. J.; Price, A. T.; Semones, M. A.; Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Tran. A. J. Am. Chem. Soc. 1993, 115, 8669-8680.
10. (b) 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, 958-964.
11. Clemens, R. J.; Hyatt, J. A. J. Org. Chem. 1985, 50, 2431-2435.
12. Regitz, M.; Maas, G. Diazo Compounds; Properties and Synthesis; Academic Press: Orlando, FL, 1986.
13. Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergammon Press: New York, 1995; Vol. 12, Chapter 5.2.
14. (a) Davis, F. A.; Wu, Y.; Xu, H.; Zhang, J. Org. Lett. 2004, 6, 4523-4525.
15. (b) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599-1602.
16. (c) Taber, D. F.; Malcolm, S. C. J. Org. Chem. 2001, 66, 944-953.
17. (d) Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113-4115.
18. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258-3260.
19. (a) Wenkert, E.; McPherson, C. A. J. Am. Chem. Soc. 1972, 94, 8084-8090.
20. (b) Sa, M. M.; Silveira, G. P.; Bortoluzzi, A. J.; Padwa, A. Tetrahedron 2003, 59, 5441-5447.
21. (c) Jiang, N.; Wang, J. Tetrahedron Lett. 2002, 43, 1285-1287.
22. Kanemasa, S.; Araki, T.; Kanai, T.; Wada, E. Tetrahedron Lett. 1999, 40, 5059-5062.
23. Moody, C. J.; Morfitt, C. N. Synthesis 1998, 1039-1042.
24. (a) Calter, M. A.; Sugathapala, P. M.; Zhu, C. Tetrahedron Lett. 1997, 38, 3837-3840.
25. (b) Calter, M. A.; Zhu, C. J. Org. Chem. 1999, 64, 1415-1419.
26. Deng, G.; Tian, X.; Qu, Z.; Wang, J. Angew. Chem., Int. Ed. 2002, 41, 2773-2776.
27. Davies, H. M. L.; Ahmed, G.; Churchill, M. R. J. Am. Chem. Soc. 1996, 118, 10774-10780.
28. (a) Mukaiyama, T. Angew. Chem. 1977, 89, 858-866.
29. (b) Mukaiyama, T. Aldrichim. Acta 1996, 29, 59-76.
30. (c) Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120.
31. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Germany, 1999; Chapter 29.
32. (e) Mukaiyama, T. Angew. Chem., Int. Ed. 2004, 43, 5590-5614.
33. (f) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137-1141.
34. Lanthanide complexes: (a) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209-211.
35. (b) Ishikawa, S.; Hamada, T.; Manabe, K.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 12236-12237.
36. Typical Mukaiyama aldol addition procedure: To a dry 5-mL round-bottomed flask fitted with a septum was added anhydrous scandium(III) triflate (14 mg, 0.030 mmol) and 3.0 mL of anhydrous dichloromethane. Vinyldiazoacetate 2 (564 mg, 2.20 mmol) was then added dropwise over 5 min, using a 1 mL syringe, followed by aldehyde (1.50 mmol). The reaction mixture was stirred at room temperature for 10 h, during which time the color of the solution changed from orrange to pale yellow. (The reactions with 1a and 1c were found to be incomplete after 6 h.) The product was isolated by flash column chromatography on silica gel, eluting with 9:1 hexane/ethyl acetate.
37. 3 produced 77% 3a, 77% 3b, 75% 3c, and 72% 3d.
38. Ramnauth, J.; Lee-Ruff, E. Can. J. Chem. 2001, 79, 114-120.
39. Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449-1483.
40. Roskamp, E. J.; Johnson, C. J. Am. Chem. Soc. 1986, 108, 6062-6063.