Intramolecular Enantioselective Palladium-Catalyzed Heck Arylation of Cyclic Enamides

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 596-602

  Ripa, Lena ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542575281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961832b     Document Type: Article

References (72)

1. For recent reviews see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7. (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
2. For recent reviews see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7. (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
3. For recent reviews see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7. (c) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
4. See for example: (a) Laschat, S.; Narjes, F.; Overman, L. E. Tetrahedron 1994, 50, 347-358. (b) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423-1430. Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393.
5. See for example: (a) Laschat, S.; Narjes, F.; Overman, L. E. Tetrahedron 1994, 50, 347-358. (b) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423-1430. Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393.
6. See for example: (a) Laschat, S.; Narjes, F.; Overman, L. E. Tetrahedron 1994, 50, 347-358. (b) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423-1430. Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365-393.
7. Sato, Y.; Sodoeka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739.
8. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846-5848.
9. (a) Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S. Tetrahedron 1989, 45, 3557-3568.
10. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1990, 46, 4003-4018.
11. (c) Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687-690. Recently the regioselectivity of related intramolecular arylations of enamides to provide polycyclic systems has been studied in some detail.
12. (d) Comins, D. L.; Baevsky, M. F.; Hong, H. J. Am. Chem. Soc. 1992, 114, 10971-10972.
13. (e) Comins, D. L.; Joseph, S. P.; Zhang, Y.-m. Tetrahedron Lett. 1996, 37, 793-796.
14. (f) Gibson, S. E., (née Thomas); Middleton, R. J. J. Chem. Soc., Chem. Commun. 1995, 1743-1744.
15. (g) Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 7834-7835.
16. (h) Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569-10582.
17. See also: (i) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938-2942.
18. Grigg, R.; Dorrity, M. J. R.; Malone, J. F.; Mongkolaussavaratana, T.; Amilaprasadh Norbert, W. D. J.; Sridharan, V. Tetrahedron Lett. 1990, 31, 3075-3076.
19. Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464-2470.
20. (a) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427.
21. (b) Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267-277.
22. (a) Bigge, C. F. Biochem. Pharmacol. 1993, 45, 1547-1561.
23. (b) Ornstein, P. L.; Monn, J. A.; Schoepp, D. D. Drug News Perspec. 1994, 7, 5-12.
24. For use of triphenylarsine in Heck reaction see: (a) Zhang, H.-C.; Daves, G. D., Jr. J. Org. Chem. 1992, 57, 4690-4696. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (c) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147-7155.
25. For use of triphenylarsine in Heck reaction see: (a) Zhang, H.-C.; Daves, G. D., Jr. J. Org. Chem. 1992, 57, 4690-4696. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (c) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147-7155.
26. For use of triphenylarsine in Heck reaction see: (a) Zhang, H.-C.; Daves, G. D., Jr. J. Org. Chem. 1992, 57, 4690-4696. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500. (c) Ripa, L.; Hallberg, A. J. Org. Chem. 1996, 61, 7147-7155.
27. In the absence of phosphine or arsine ligands (see ref 10c) a slow reaction was encountered. Addition of triphenylphosphine, tri-o-tolylphosphine, or tri-2-furylphosphine gave mixtures of double bond isomers.
28. The beneficial effect of silver additives in controlling double bond isomerization in the Heck reaction was first observed by Overman's group.
29. (a) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133.
30. (b) Abelman, M. M.; Oveman, L. E. J. Am. Chem. Soc. 1988, 110, 2328-2329.
31. For use of silver salts in controlling double bond isomerization in heterocycles see: (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (f) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848. (g) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015-4017. See also refs 7 and 10c.
32. For use of silver salts in controlling double bond isomerization in heterocycles see: (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (f) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848. (g) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015-4017. See also refs 7 and 10c.
33. For use of silver salts in controlling double bond isomerization in heterocycles see: (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (f) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848. (g) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015-4017. See also refs 7 and 10c.
34. For use of silver salts in controlling double bond isomerization in heterocycles see: (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (f) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848. (g) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015-4017. See also refs 7 and 10c.
35. For use of silver salts in controlling double bond isomerization in heterocycles see: (c) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (d) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050. (e) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. (f) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848. (g) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015-4017. See also refs 7 and 10c.
36. For a related example see ref 5a.
37. BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350.
38. Prolonged reaction times do not alter the product distribution.
39. (R)-2a and (R)-2b carry the aryl ring on opposite side of the tetrahydropyridine ring. See ref 27.
40. The counter anion of the silver salts has been reported to influence the chiral induction in asymmetric Heck reactions.
41. (a) Sato, Y.; Sodoeke, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954.
42. (b) Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 4965-4968.
43. (c) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371-382.
44. A combination of silver phosphate and calcium carbonate was used by Shibasaki to obtain high enantiomeric excess, see ref 17a.
45. (a) Ashimori, A.; Overman, L. E. J. Org. Chem. 1992, 57, 4571-4572. Applying Overman's conditions omitting silver additives and with 1,2,2,6,6-pentamethylpiperidine as base rendered racemic products.
46. (b) Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6949-6951.
47. Ozawa and Hayashi found that the kinetic resolution process was promoted by acetate ions displacing the olefin from the π-complex. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
48. Employing sterically hindered amine bases (1,2,2,6,6-penta-methylpiperidine and diisopropylethylamine) reduced the formation of the undesired reduction product but furnished lower yields and moderate asymmetric induction of 2a (ee < 40%).
49. 3.
50. Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796-5800. See also ref 2a.
51. (a) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202.
52. See also: (b) Pfaltz, A. Acta Chem. Scand. 1996, 50, 189-194.
53. The systematic name of (S)-8 is ( - )-(S)-4-tert-butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydrooxazole.
54. (a) Koch, G.; Lloyd-Jones, G. C.; Loiseleur, O.; Pfaltz, A.; Prétôt, R.; Schaffner, S.; Schnider, P.; von Matt, P. Recl Trav. Chim. Pays-Bas 1995, 114, 206-210.
55. (b) Peer, M.; de Jong, J. C.; Kiefer, M.; Langer, T.; Rieck, H.; Schell, H.; Sennhenn, P.; Sprintz, J.; Steinhagen, H.; Wiese, B.; Helmchen, G. Tetrahedron 1996, 52, 7547-7583.
56. Using (S)-8 as ligand in cyclization reactions starting from aryl iodide 1a in DMAA with silver phosphate resulted in racemic 3a as the major product.
57. Ripa, L.; Hallberg, A.; Sandström, J. Manuscript in preparation.
58. Compounds 3a and 6a were resolved on columns packed with swollen microcrystalline triacetylcellulose (TAG), packed and provided by Dr Roland Isaksson, Department of Analytical Pharmaceutical Chemistry, Box 574, Uppsala University, BMC, SE-751 23 Uppsala, Sweden, see: Isaksson, R.; Erlandsson, P.; Hansson, L.; Holmberg, A.; Berner, S. J. Chromatogr. 1990, 498, 257-280.
59. 2 as carrier gas and a flame ionization detector. Compounds 2a, 3a, 4a, and 6a were separated on a column coated with 50% heptakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-cydodextrin in OV 1701 and compound 2b on a column coated with 20% octakis(2,6-di-O-methyl-3-O-pentyl)-γ-cyclodextrin in OV 1701, prepared and developed by Prof. W. A. König, Institut für Organische Chemie, Universität Hamburg, D-201 46 Hamburg, Germany.
60. chemical equation presented.
61. Meyers, A. I.; Edwards, P. D.; Bailey, T. R.; Jagdmann, G. E. J. J. Org. Chem. 1985, 50, 1019-1026.
62. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
63. For the related intermolecular arylation of 2,3-dihydrofuran, see: (a) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (b) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. See also ref 19.
64. For the related intermolecular arylation of 2,3-dihydrofuran, see: (a) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (b) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. See also ref 19.
65. 2[(R)-BINAP], see ref 20.
66. Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497-526.
67. For a discussion of hard and soft acids and bases coordinating to soft Pd(II), see: (a) Davies, J. A.; Hartley, F. R. Chem. Rev. 1981, 81, 79-90. See also: (b) Clark, G. R.; Palenik, G. J. Inorg. Chem. 1970, 9, 2754-2760. Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937-1948.
68. For a discussion of hard and soft acids and bases coordinating to soft Pd(II), see: (a) Davies, J. A.; Hartley, F. R. Chem. Rev. 1981, 81, 79-90. See also: (b) Clark, G. R.; Palenik, G. J. Inorg. Chem. 1970, 9, 2754-2760. Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937-1948.
69. For a discussion of hard and soft acids and bases coordinating to soft Pd(II), see: (a) Davies, J. A.; Hartley, F. R. Chem. Rev. 1981, 81, 79-90. See also: (b) Clark, G. R.; Palenik, G. J. Inorg. Chem. 1970, 9, 2754-2760. Dekker, G. P. C. M.; Buijs, A.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M.; Smeets, W. J. J.; Spek, A. L.; Wang, Y. F.; Stam, C. H. Organometallics 1992, 11, 1937-1948.
70. van Leeuwen, P. W. N. M.; Roobeek, C. F.; van der Heijden, H. J. Am. Chem. Soc. 1994, 116, 12117-12118. See also ref 36c.
71. The molecular model analyses were based on the X-ray structure of a π-allyl palladium complex with a similar ligand published previously. Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Hutter, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-1526.
72. Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477-8478.