Diastereoselection in the formation of contiguous quaternary carbon stereocenters by the intramolecular Heck reaction

Journal of Organic Chemistry

Volumn 71, Issue 7, 2006, Pages 2600-2608

  Overman, Larry E ^a   Watson, Donald A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; INTRAMOLECULAR HECK REACTION; QUATERNARY STEREOCENTERS; SPIROOXINDOLE RING;

CARBON; CARBONYLATION; DEMONSTRATIONS; MOLECULAR DYNAMICS; ORGANIC COMPOUNDS; SUBSTITUTION REACTIONS; SUBSTRATES;

STEREOCHEMISTRY;

CARBONYL DERIVATIVE; CYCLOHEXENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; HECK REACTION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

CARBON; CYCLIZATION; CYCLOHEXENES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 33645500606     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0523363     Document Type: Article

References (55)

1. Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702-7003.
2. Overman, L. E.; Watson, D. A. J. Org. Chem. 2006, 71, 2587-2599.
3. Peterson, E. A.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11943-11948.
4. Piers, E.; Cheng, K. F.; Nagakura, I. Can. J. Chem. 1982, 60, 210-223.
5. Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1974, 15, 4319-4322.
6. For leading references to hydroxy-directed reductions of ketones, see: Gribble, G. W. Sodium Triacetoxyborohydride. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley & Sons: New York, 1995; Vol. 7, pp 4649-4653.
7. For a previous synthesis of this intermediate, see: Banwell, M. G.; Lambert, J. N.; Richards, S. L. Aust. J. Chem. 1991, 44, 939-950.
8. Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1986, 37, 3931-3934.
9. Bald, E.; Saigo, K.; Mukaiyama, T. Chem. Lett. 1975, 1163-1166.
10. (a) Cai, J.; Davison, B. E.; Ganellin, C. R.; Thaisrivongs, S. Tetrahedron Lett. 1995, 36, 6535-6536.
11. (b) Larson, G. L.; Hernandez, A. J. Org. Chem. 1973, 38, 3935-3936.
12. (c) Rollin, P.; Pougny, J. R. Tetrahedron 1986, 42, 3479-3490.
13. (d) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358.
14. Heating was required for this transformation; at room temperature, only mono- and diprotected mixed methoxy ketals were isolated for this class of diols.
15. The acetonide of bromide 5 could also be prepared using this method in 67% yield. For details, see: Watson, D. A. Investigation into the Origins of Diastereoselection in Spirocyclic Oxindole Forming Intramolecular Heck Cyclizations. Ph.D. Thesis, University of California-Irvine, Irvine, CA, 2004.
16. Laganis, E. D.; Chenard, B. L. Tetrahedron Lett. 1984, 25, 5831-5834.
17. Gassman, P. G.; Schenck, W. N. J. Org. Chem. 1977, 42, 918-920.
18. (a) Liotta, C.; Markiewicz, W.; Santiesteban, H. Tetrahedron Lett. 1977, 18, 4365-4368.
19. (b) Fisher, J. W.; Trinkle, K. L. Tetrahedron Lett. 1994, 35, 2505-2508.
20. Salomon, C. J.; Mata, E. G.; Mascartti, O. A. Tetrahedron Lett. 1991, 32, 4239-4242.
21. For leading references on the enzymatic cleavage of methyl esters, see: Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley and Sons: New York, 1999; p 385.
22. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 48, 4171-4174.
23. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U. H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461-5464.
24. Benzyl esters 13a, 13b, 18a, and 18b were prepared in analogous fashion to their methyl ester congeners. See ref 2 and Supporting Information for details.
25. Hydrogenation of the alkene was not observed in this transformation after short reaction times.
26. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
27. Costa, J.; Frerot, E.; Jouin, P.; Castro, B. Tetrahedron Lett. 1991, 32, 1967-1970.
28. Carpino, L. A.; El-Faham, A. J. Am. Chem. Soc. 1995, 117, 5401-5402.
29. Lee, J. B. J. Am. Chem. Soc. 1966, 88, 3440-3441.
30. Diago-Meseguer, J.; Palomo-Coll, A. L.; Fernandez-Lizarbe, J. R.; Zugaza-Bilbao, A. Synthesis 1980, 547-551.
31. Stearns, B. A. A Formal Synthesis of Loracarbef and Total Synthesis of Polypyrrolidinoindoline Alkaloids. Ph.D. Thesis, University of California-Irvine, Irvine, CA, 2000.
32. See Supporting Information for details.
33. The low yield of this minor product, and the limited amounts of starting material available, prevented successful isolation.
34. For examples of palladium-mediated reactions terminated by β-alkoxide eliminations, see: (a) Hacksell, U.; Daves, G. D., Jr. Organometallics 1983, 2, 772-775.
35. (b) Saito, S.; Hara, T.; Takahashi, N.; Hirai, M.; Moriwake, T. Synlett 1992, 237-238.
36. (c) Daun, J.; Cheng, C. Tetrahedron Lett. 1993, 34, 4019-4022.
37. (d) Hosokawa, T.; Sugafugi, T.; Yamanaka, T.; Murahashi, S. J. Organomet. Chem. 1994, 470, 253-255.
38. (e) Moinet, C.; Fiaud, J. Tetrahedron Lett. 1995, 36, 2051-2052.
39. (f) Bejeguelal, K.; Joseph, L.; Bolitt, V.; Sinou, D. J. Carbohydr. Chem. 2000, 19, 221-232.
40. The cyclizations of oxindoles 17b and 21b proceeded more slowly than the previous substrates; after 24 h, significant quantities of starting material remained (ca. 15-20%). Upon heating the mixture for 30 h, the remaining starting material had been reduced to about 3-5%.
41. 8.
42. Overman, L. E.; Larrow, J. F.; Stearns, B. A.; Vance, J. M. Angew. Chem., Int. Ed. 2000, 39, 213-215.
43. 2
44. Because of steric interactions, trans-vicinal siloxy groups destabilize the diequatorial conformation, making it energetically similar to the diaxial conformation. See: Marzabadi, C. H.; Anderson, J. E.; Gonzalez-Outeirino, J.; Gaffney, P. R. J.; White, C. G. H.; Tocher, D. A.; Todaro, L. J. J. Am. Chem. Soc. 2003, 125, 15163-15173.
45. Coordination-controlled Heck reactions have been suggested for various Lewis basic functional groups. For examples, see: (a) Earley, W. G.; Oh, T.; Overman, L. E. Tetrahedron Lett. 1988, 29, 3785-3788.
46. (b) Madin, A.; Overman, L. E. Tetrahedron Lett. 1992, 33, 4859-4862.
47. (c) Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217-8225.
48. (d) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamel, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577-11585.
49. (e) Buezo, N. D.; de la Rosa, J. C.; Priego, J.; Alonso, I.; Carretero, J. C. Chem.-Eur. J. 2001, 7, 3890-3900.
50. (f) Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2003, 125, 3430-3431.
51. (g) Oestreich, M.; Sempere-Culler, F.; Machotta, A. B. Angew. Chem., Int. Ed. 2005, 44, 149-152.
52. (h) Osetreich, M. Eur. J. Org. Chem. 2005, 783-792.
53. (a) General experimental details have been described: MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033-9044.
54. (b) CCDC 288976-288978 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
55. On occasion, Pd black was deposited toward the end of the reaction.