Rhodium-catalyzed synthesis of 3-hydroxy-β-lactams via oxonium ylide generation: Three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8421-8424

  Alcaide, Benito ^a   Almendros, Pedro ^b   Aragoncillo, Cristina ^a   Callejo, Ricardo ^a   Ruiz, M Pilar ^a   Torres, M Rosario ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINES; CHEMICAL EQUATIONS; ETHYL DIAZOACETATE; OXONIUM; RHODIUM-CATALYZED; RHODIUM-CATALYZED SYNTHESIS; SINGLE CRYSTAL X-RAY DIFFRACTION; SINGLE-STEP; STEREOGENIC CENTERS; THREE COMPONENT REACTIONS;

AMIDES; ORGANIC POLYMERS; RHODIUM; SINGLE CRYSTALS; STEREOSELECTIVITY;

COMPLEXATION;

ALCOHOL; AZETIDINE DERIVATIVE; BETA LACTAM DERIVATIVE; DIAZOACETIC ACID ETHYL ESTER; RHODIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

ALCOHOLS; AZETIDINES; CATALYSIS; DIAZONIUM COMPOUNDS; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; RHODIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 70350736017     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9019013     Document Type: Article

References (51)

1. (a) Unkefer, C. J.; London, R. E.; Durbin, R. D.; Uchytil, T. F.; Langston-Unkefer, P. J. J. Biol. Chem. 1987, 262, 4993.
2. (b) Meek, T. D.; Villafranca, J. V. Biochemistry 1980, 19, 5513.
3. (c) Sinden, S. L.; Durbin, R. D. Nature 1968, 219, 379.
4. Benfatti, F.; Cardillo, G.; Gentilucci, L.; Perciccante, R.; Tolomelli, A.; Catapano, A. J. Org. Chem. 2006, 71, 9229.
5. Imada, A.; Gitano, K.; Kintana, K.; Muroi, M.; Asai, M. Nature 1981, 289, 590.
6. (a) Dolle, R. E.; Hughes, M. J.; Li, C.-S.; Kruse, L. I. J. Chem. Soc., Chem. Commun. 1989, 1448.
7. (b) Greenlee, W. J.; Springer, J. P.; Patchett, A. A. J. Med. Chem. 1989, 32, 165.
8. (c) Baldwin, J. E.; Otsuka, M.; Wallce, P. M. Tetrahedron 1986, 42, 3097.
9. As an example, (2R,3S)-3-amino-2-hydroxy-5-methylhexanoic acid (norstatine) and (3R,4S)-4-amino-3-hydroxy-5-methylheptanoic acids (statine) are residues for peptide inhibitors of enzymes such as rennin and HIV protease. For rennin, see: Thaisrivongs, S.; Pals, D. T.; Kroll, L. T.; Turner, S. R.; Han, F.-S. J. Med. Chem. 1987, 30, 976.
10. For HIV protease, see: Huff, J. R. J. Med. Chem. 1991, 34, 2305.
11. (a) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.
12. (b) Wee, A. G. H. Curr. Org. Synth. 2006, 3, 499.
13. For carbonyl ylides, see: (a) Doyle, M. P.; Mckervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, 1998.
14. (b) Li, A. H.; Dai, L. X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
15. (c) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
16. (d) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
17. For phosphonium ylides, see: (e) Aggarwal,V. K.; Fulton, J. R.; Sheldon, C. G.; Vicente, J. D. J. Am. Chem. Soc. 2003, 125, 6034.
18. (f) Maryanoff, B. E.; Retiz, A. B. Chem. Rev. 1989, 89, 863.
19. For oxonium ylides, see: (g) Tester, R. W.; West, F. G. Tetrahedron Lett. 1998, 39, 4631.
20. (h) West, F. G.; Eberlein, T. H.; Tester, R. W. J. Chem. Soc., Perkin Trans. 1 1993, 2857.
21. (i) Pirrung, M. P.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060.
22. (j) Padwa, A.; Hornbuckle, S. F.; Fryxell, G. E.; Stull, P. D. J. Org. Chem. 1989, 54, 817.
23. For ammonium ylides, see: (k) West, F. G.; Naidu, B. N. J. Am. Chem. Soc. 1993, 115, 1177.
24. (l) Doyle, M. P.; Bagheri, V.; Claxton, E. E. J. Chem. Soc., Chem. Commun. 1990, 46.
25. (m) Doyle, M. P.; Tamblyn, W. H.; Bagheri, V. J. Org. Chem. 1981, 46, 5094.
26. For reviews of multicomponent reaction, see: (a) Touré, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439.
27. (b) Ganem, B. Acc. Chem. Res. 2009, 42, 463.
28. (c) Guillena, G.; Ramón, D. J.; Yus, M. Tetrahedron: Asymmetry 2007, 18, 693.
29. (d) Dömling, A. Chem. Rev. 2006, 106, 17.
30. (e) Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Streekenth, A. R.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.
31. (f) Multicomponent Reactions: Zhu, J., Bienaymé, H., Eds.; Wiley: Weinheim, Germany, 2005.
32. (a) Zhu, Y.; Zhai, C.; Yue, Y.; Yang, L.; Hu, W. Chem. Commun. 2009, 1362.
33. (b) Hu, W.; Xu, X.; Zhou, J.; Liu, W.-J.; Huang, H.; Hu, J.; Yang, L.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 7782.
34. (c) Huang, H.; Guo, X.; Hu, W. Angew. Chem., Int. Ed. 2007, 46, 1337.
35. (d) Guo, X.; Huang, H.; Yang, L.; Hu, W. Org. Lett. 2007, 9, 4721.
36. (e) Lu, C.; Liu, H.; Chen, Z.; Hu, W.; Mi, A. Org. Lett. 2005, 7, 83.
37. (f) Huang, H.; Wang, Y.; Chen, Z.; Hu, W. Adv. Synth. Catal. 2005, 347, 531.
38. (g) Wang, Y.; Chen, Z.; Mi, A.; Hu, W. Chem. Commun. 2004, 2486.
39. (h) Wang, Y.; Zhu, Y.; Chen, Z.; Mi, A.; Hu, W.; Doyle, M. P. Org. Lett. 2003, 5, 3923.
40. See, for instance: (a) Alcaide, B.; Almendros, P.; Martínez del Campo, T.; Quirós, M. T. Chem. - Eur. J. 2009, 15, 3344.
41. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Cabrero, G.; Callejo, R.; Ruiz, M. P. Eur. J. Org. Chem. 2008, 4434.
42. (c) Alcaide, B.; Almendros, P.; Martínez del Campo, T. Angew. Chem., Int. Ed. 2007, 46, 6684.
43. (d) Alcaide, B.; Almendros, P.; Martínez del Campo, T.; Rodríguez-Acebes, R. Adv. Synth. Catal. 2007, 349, 749.
44. (e) Alcaide, B.; Almendros, P.; Cabrero, G.; Ruiz, M. P. Chem. Commun. 2007, 4788.
45. (a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2001, 66, 5208.
46. For a review on the chemistry of azetidine-2,3-diones, see: (b) Alcaide, B.; Almendros, P. Org. Prep. Proced. Int. 2001, 33, 315.
47. Alcaide, B.; Almendros, P.; Carrascosa, R.; Redondo, M. C. Chem. - Eur. J. 2008, 14, 637.
48. Lu, C.-D.; Liu, H.; Chen, Z.-Y.; Hu, W.-H.; Mi, A.-Q. Chem. Commun. 2005, 2624.
49. Selected NOE enhancements are collected in the Supporting Information. NOE irradiation of H3′ in syn-(+)-4a resulted in enhancement of the signal corresponding to H4 (3%). Conversely, the same NOE enhancement was observed for H3′ upon irradiation of H4, which is consistent with a syn relative stereochemistry between H4 and H3′ and R configuration at C3′. A NOE enhancement of 0.2% for H4 in anti-(+)-4a on irradiating the signal corresponding to H3′ is in good agreement with an anti relative disposition between H3′ and H4 in anti-(+)-4a (S configuration at the new stereogenic center at C3′).
50. 2 (SHELXL-97). The non-hydrogen atoms were refined anisotropically. The hydrogen atomswere refined only in terms of their coordinates.CCDC-739823 contains the supplementary crystallographic data for this paper.These data can be obtained free of charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/deposit.
51. 2 (SHELXL-97). The non-hydrogen atoms were refined anisotropically. The hydrogen atoms were refined only in terms of their coordinates. CCDC-739824 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/deposit.