Stereocontrolled synthesis of contiguous C(sp3) - C(aryl) bonds by lanthanide(III)-catalyzed domino aryl-claisen [3,3]-sigmatropic rearrangements

Organic Letters

Volumn 12, Issue 20, 2010, Pages 4446-4449

  Ramadhar, Timothy R ^a   Kawakami, Jun Ichi ^a   Lough, Alan J ^a   Batey, Robert A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOALKANE DERIVATIVE; ETHER DERIVATIVE; LANTHANIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

ALKENES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLOPARAFFINS; ETHERS; LANTHANOID SERIES ELEMENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77957832399     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1018147     Document Type: Article

References (53)

1. Domino Reactions in Organic Synthesis; Tietze, L. F., Brasche, G., Gericke, K., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
2. The Claisen Rearrangement: Methods and Applications; Hiersemann, M., Nubbemeyer, U., Eds.; Wiley-VCH: Weinheim, Germany, 2007.
3. Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Chem. Soc. Rev. 2010, 38, 3133-3148
4. Martin Castro, A. M. Chem. Rev. 2004, 104, 2939-3002
5. Chai, Y.; Hong, S.; Lindsay, H. A.; McFarland, C.; McIntosh, M. C. Tetrahedron 2002, 58, 2905-2928
6. Lutz, R. P. Chem. Rev. 1984, 84, 205-247
7. Paquette, L. A. Tetrahedron 1997, 41, 13971-14020
8. Al-Maharik, N.; Botting, N. P. Tetrahedron 2003, 59, 4177-4181
9. Sauer, E. L. O.; Barriault, L. Org. Lett. 2004, 6, 3329-3332
10. Curran, D. P.; Suh, Y. G. J. Am. Chem. Soc. 1984, 106, 5002-5004
11. Curran, D. P.; Suh, Y. G. Tetrahedron Lett. 1984, 25, 4179-4182
12. Curran, D. P.; Suh, Y. G. Carbohydr. Res. 1987, 171, 161-191
13. Majumdar, K. C. Synlett 2008, 16, 2400-2411
14. Hiratani, K.; Albrecht, M. Chem. Soc. Rev. 2008, 37, 2413-2421
15. Hwang, B. Y.; Su, B.-N.; Chai, H.; Mi, Q.; Kardono, L. B. S.; Afriastini, J. J.; Riswan, S.; Santarsiero, B. D.; Mesecar, A. D.; Wild, R.; Fairchild, C. R.; Vite, G. D.; Rose, W. C.; Farnsworth, N. R.; Cordell, G. A.; Pezzuto, J. M.; Swanson, S. M.; Kinghorn, A. D. J. Org. Chem. 2004, 69, 3350-3358
16. Tamiya, M.; Jäger, C.; Ohmori, K.; Suzuki, K. Synlett 2007, 5, 780-784
17. Khan, R.; Malik, A.; Adhikari, A.; Qadir, M. I.; Choudhary, M. I. Chem. Pharm. Bull. 2009, 57, 415-417
18. Ogata, T.; Yahara, X.; Hisatsune, R.; Konishi, R.; Nohara, T. Chem. Pharm. Bull. 1990, 38, 2750-2755
19. Wada, S.; Yasui, Y.; Hitomi, T.; Tanaka, R. J. Nat. Prod. 2007, 70, 1605-1610
20. Recent examples include: stepwise C-glycoside formation, followed by phenol addition and [3,3]-sigmatropic rearrangement, see
21. Yeager, A. R.; Min, G. K.; Porco, J. A., Jr.; Schaus, S. E. Org. Lett. 2006, 8, 5065 - 5068.
22. 3) bonds infused 2,3-dihydrofurans (non-enantioselective), see: Wang, Q.-F.; Hou, H.; Hui, L.; Yan, C.-G. J. Org. Chem. 2009, 74, 7403-7406
23. An enantioselective Pd-catalyzed cyclization of propargylic carbonates with 2-(2-hydroxyphenyl)acetates, see: Yoshida, M.; Higuchi, M.; Shishido, K. Org. Lett. 2009, 11, 4752 - 4755.
24. For examples on the use of the Ireland - Claisen rearrangement to afford these moieties through the formation of a ?-bond between two non-aryl carbon atoms, see
25. Corey, E. J.; Lee, D.-Y. J. Am. Chem. Soc. 1991, 113, 4026-4028
26. Lee, E. E.; Batey, R. A. Angew. Chem., Int. Ed. 2004, 43, 1865-1868
27. Lee, E. E.; Batey, R. A. J. Am. Chem. Soc. 2005, 127, 14887-14893
28. Rodrigues, A.; Lee, E. E.; Batey, R. A. Org. Lett. 2010, 12, 260-263
29. Zapf, A.; Beller, M.; Riermeier, T. H. Transition Metals for Organic Synthesis, 2nd ed.; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 231 - 256.
30. Chan, D. M. T.; Lam, P. Y. S. Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine; Hall; D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 205 - 240.
31. Frlan, R.; Kikelj, S. Synthesis 2006, 14, 2271-2285
32. Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381-1384
33. Racemic and enantiopure synthesis of 1a
34. Demay, S.; Kotschy, A.; Knochel, P. Synthesis 2001, 6, 863-866
35. Lüssem, B. J.; Gais, H.-J. J. Am. Chem. Soc. 2003, 125, 6066-6067
36. Fujimoto, I.; Mita, T.; Maki, K.; Shiro, M.; Sata, A.; Furusho, S.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 16438-16439
37. Sabol, J. S.; Cregge, R. J. Tetrahedron Lett. 1989, 30, 3377-3380
38. See the Supporting Information for details.
39. NAr procedure: Adams, S. R.; Kao, J. P. Y.; Grynkiewicz, G.; Minta, A.; Tsien, R. Y. J. Am. Chem. Soc. 1988, 110, 3212-3220
40. Stadler, A.; Kappe, C. O. Microwave Assisted Organic Synthesis; Lidström, P.; Tierney, J. P., Eds.; Blackwell Publishing: Oxford, England, 2005; p 206.
41. Gignere, R. J.; Bray, T.; Duncan, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945-4948
42. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 815-816
43. 3-catalyzed aryl-Claisen rearrangements, see
44. Gester, S.; Metz, P.; Zierau, O.; Vollmer, G. Tetrahedron 2001, 57, 1015-1018
45. Tischer, S.; Metz, P. Adv. Synth. Catal. 2007, 349, 147-151
46. Hayashi, T.; Yamasaki, K.; Mimura, M.; Uozumi, Y. J. Am. Chem. Soc. 2004, 126, 3036-3037
47. Reaction conditions were modified from ref 19c.
48. 3 were required. We consider the use of much lower catalyst loadings and the use of a more environmentally benign solvent to be a preferable protocol.
49. CCDC 716574 and 716575 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html.
50. Yu, X.-Q.; Yoshimura, F.; Ito, F.; Sasaki, M.; Hirai, A.; Tanino, K.; Miyashita, M. Angew. Chem., Int. Ed. 2008, 47, 750-754
51. Marvell, E. N.; Stephenson, J. L. J. Org. Chem. 1960, 25, 676-677
52. Marvell, E. N.; Stephenson, J. L.; Ong, J. J. Am. Chem. Soc. 1965, 87, 1267-1274
53. Goering, H. L.; Kimoto, W. I. J. Am. Chem. Soc. 1965, 87, 1748-1752