Catalytic asymmetric synthesis of quaternary carbon centers. Exploratory investigations of intramolecular heck reactions of (E)-α,β-unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products

Journal of the American Chemical Society

Volumn 120, Issue 26, 1998, Pages 6477-6487

  Ashimori, Atsuyuki ^a,b   Bachand, Benoit ^a,c   Overman, Larry E ^a   Poon, Daniel J ^a,d  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Green Cross Company   (South Korea)

^c BioChem Therapeutique Inc   (Canada)

^d Immunology and Pathology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CATALYST; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; TECHNIQUE;

EID: 0032496952     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980786p     Document Type: Article

References (51)

1. (a) Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
2. (b) Heck, R. F.; Nolley, J. P., Jr. J Org. Chem. 1972, 37, 2320.
3. One indication of the importance of the Heck reaction is seen in the large number of recent reviews. For selected examples, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 249-252. (c) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447. (d) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
4. One indication of the importance of the Heck reaction is seen in the large number of recent reviews. For selected examples, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 249-252. (c) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447. (d) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
5. One indication of the importance of the Heck reaction is seen in the large number of recent reviews. For selected examples, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 249-252. (c) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447. (d) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
6. One indication of the importance of the Heck reaction is seen in the large number of recent reviews. For selected examples, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (b) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 249-252. (c) Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth. 1996, 3, 447. (d) Bräse, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 3.
7. (a) Grigg, R.; Sridharan, V.; Stevenson, P.; Worakan, T. J. Chem. Soc., Chem. Commun. 1986, 1697.
8. (b) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130.
9. The application of intramolecular Heck reactions in natural products synthesis has been recently reviewed: Link, J. T.; Overman, L. E. In Metal-catalyzed Cross-coupling Reactions; Diederick, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 6.
10. For recent reviews, see: (a) Shibasaki, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 119-151. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
11. For recent reviews, see: (a) Shibasaki, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, 1996; pp 119-151. (b) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
12. Heck, R. F. Organic Reactions 1982, 27, 345-390.
13. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738.
14. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846.
15. Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813.
16. (b) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423.
17. Early parts of these investigations were described in a preliminary communication: Ashimori, A.; Overman, L. E. J. Org. Chem. 1992, 57, 4571.
18. Ashimori, A.; Bachand, B.; Govek, S.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488-6499.
19. For a preliminary communication, see: Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6949.
20. For a preliminary communication, see: Overman, L. E.; Poon, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 518.
21. Matsuura, T.; Overman, L. E.; Poon, D. J. Am. Chem. Soc. 1998, 120, 6500-6503.
22. Iio, H.; Isobe, M.; Kawai, T.; Goto, T. Tetrahedron 1979, 35, 941.
23. (a) Lindgren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888.
24. (b) Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2901.
25. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417.
26. Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1953.
27. Lebedinskiî, V. V.; Simanovskiî, P. V.; Slutsker, O. D. Izvest. Sektora Platiny i Drugikh Blagorodnykh Metal., Inst. Obshcheî Neorg. Khim., Akad. Nauk S.S.S.R. 1948, 43. Chem. Abstr. 1950, 44, 9293.
28. Lebedinskiî, V. V.; Simanovskiî, P. V.; Slutsker, O. D. Izvest. Sektora Platiny i Drugikh Blagorodnykh Metal., Inst. Obshcheî Neorg. Khim., Akad. Nauk S.S.S.R. 1948, 43. Chem. Abstr. 1950, 44, 9293.
29. (a) Ukai, T.; Kawazura, H.; Ishii, Y. J. Organomet. Chem. 1974, 65, 253.
30. (b) Pierpont, C. G.; Mazza, M. C. Inorg. Chem. 1974, 13, 1891.
31. Quast, H.; Risler, W.; Doellscher, G. Synthesis 1972, 558.
32. (a) Barton, D. H. R.; Elliott, J. D.; Gero, S. D. J. Chem. Soc., Perkin Trans. 1 1982, 2085.
33. (b) Corey, E. J.; Jardine, P. D. S.; Mohri, T. Tetrahedron Lett. 1988, 29, 6409.
34. (a) Absolute configuration was assigned by the method of Rogers: Rogers, D. Acta Crystallogr. 1981, A37, 734.
35. (b) 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, 12 Union Road, Cambridge, CB2 1EZ, UK.
36. Zumbrunn, A.; Uebelhart, P.; Eugster, C. H. Helv. Chim. Acta 1985, 68, 1519.
37. Kende, A. S.; Fludzinski, P. Org. Synth. 1986, 64, 104.
38. Lipton, M. F.; Basha, A.; Weinreb, S. M. Org. Synth. 1978, 59, 49.
39. Kim, K. D.; Magriotis, P. A. Tetrahedron Lett. 1990, 31, 6137.
40. MacInnes, I.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 1987, 1077.
41. Collier, W. L.; Macomber, R. S. J. Org. Chem. 1973, 38, 1367.
42. Koji, A.; Ono, N.; Saito, T.; Tanaka, K.; Yamada, T. Bull. Chem. Soc. Jpn. 1978, 51, 2401.
43. Rossi, R.; Carpita, A.; Cossi, P. Tetrahedron 1992, 48, 8801.
44. Dauben, W. G.; Lorber, M.; Fullerton, D. S. J. Org. Chem. 1969, 34, 3587.
45. Kabalka, G. W.; Hutchins, R.; Natale, N. R.; Yang, D. T. C.; Broach, V. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 293.
46. Ohno, K.; Tsuji. J. Synthesis 1969, 157.
47. Brannock, K. C.; Dietl, H. K. Tetrahedron Lett. 1973, 1273.
48. Barton deoxygenation of the xanthate derivative and Wolf-Kishner reduction of the tosylhydrazone derivative failed. Attempts to prepare the tosylate or iodide derivative of the corresponding primary alcohol, as a prelude to reduction, were also unsuccessful.
49. Claremon, D. A.; Magolda, R. L.; Nicolaou, K. C. J. Am. Chem. Soc. 1980, 102, 2, 1404.
50. 3 and BINAP were purchased from Aldrich Chemical Co. High-resolution mass spectra were measured on a MicroMass Analytical 7070E spectrometer (EI or CI-isobutane); uncertainty (s) in mass measurements is 1.0 millimass unit (molecular weight < 400) or 1.5 millimass units (molecular weight 400-1000). Other general experimental details have been described: Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241.
51. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.