N-Functionalized 1-Alkynylamides: New Building Blocks for Transition Metal Mediated Inter- and Intramolecular [2+2+1] Cycloadditions

Angewandte Chemie - International Edition

Volumn 37, Issue 4, 1998, Pages 489-492

  Witulski, Bernhard ^a   Stengel, Thomas ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Alkynes; Carbenes; Cobalt; Cycloadditions; Heterocycles

Indexed keywords

EID: 0032473436     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980302)37:4<489::aid-anie489>3.3.co;2-e     Document Type: Article

References (53)

1. a) H.-W. Frühauf, Chem. Rev. 1997, 97, 523-596;
2. b) M. Lautens, W. Klute, W. Tam, ibid. 1996, 96, 49-92;
3. c) D. F. Harvey, D. M. Sigano, ibid. 1996, 96, 271-288;
4. d) E. Negishi, C. Copéret, S. Ma, S.-Y. Liou, F. Liu, ibid. 1996, 96, 365-393;
5. e) I. Ojima, M. Tzamarioudaki, Z. Li, R. J. Donovan, ibid. 1996, 96, 635-662;
6. f) Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim, 1995;
7. g) N. E. Schore. Chem. Rev. 1988, 88, 1081-1119.
8. a) G. Himbert, Methoden Org. Chem. (Houben-Weyl), 1993, Vol. E15, p. 3267-3461;
9. b) J. Collard-Motte, Z. Janousek, Top. Curr. Chem. 1986, 130, 89-132;
10. c) G. Pitacco, E. Valentin in The Chemistry of Amino, Nitroso and Nitro Compounds and their Derivatives, Supplement F, Part 1 (Ed.: S. Patai), Wiley, Chichester, UK, 1982, p. 624-714;
11. d) J. Ficini, Tetrahedron 1976, 32, 1448-1486.
12. a) A. Padwa, Y. Gareau, B. Harrison, A. Rodriguez, J. Org. Chem. 1992, 57, 3540-3545;
13. b) D. L. Boger, M. Patel in Prog. Heterocycl. Chem. 1988, 1, 30-60.
14. a) J. Ficini, J. Organomet. Chem. 1979, 177, 265-272;
15. b) K. H. Dötz, I. Pruskil, Chem. Ber. 1978, 111, 2059-2063;
16. c) J. Ficini, J. d'Angelo, S. Falou, Tetrahedron Lett. 1977, 1645-1648;
17. d) J. Ficini, ibid. 1979, 1499-1502.
18. a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178;
19. b) synthesis: P. J. Stang in ref. [1 f] p. 67-98.
20. a) K. S. Feldman, M. M. Bruendl, K. Schildknegt, A. C. Bohnstedt, J. Org. Chem. 1996, 61, 5440-5452;
21. b) K. Schildknegt, A. C. Bohnstedt, K. S. Feldman, A. Sambandam, J. Am. Chem. Soc. 1995, 117, 7544-7545.
22. a) W. Kirmse, Angew. Chem. 1997, 109, 1212-1218; Angew. Chem. Int. Ed. Engl. 1997, 36, 1164-1170;
23. a) W. Kirmse, Angew. Chem. 1997, 109, 1212-1218; Angew. Chem. Int. Ed. Engl. 1997, 36, 1164-1170;
24. b) R. Walsh, S. Untiedt, M. Stohlmeier, A. de Meijere, Chem. Ber. 1989, 122, 637-642;
25. c) J. J. W. McDouall, H. B. Schlegel, J. S. Francisco, J. Am. Chem. Soc. 1989, 111, 4622-4627.
26. 13C NMR, IR spectroscopy, mass spectrometry, C,H,N analysis and/or high-resolution mass spectrometry.
27. 3) of the acetylene carbon atoms of the 1-alkynylamides: 4b: δ = 95 (s), 74 (s); 4c: δ = 91 (s), 76 (s); 4d: δ = 92 (s), 78 (s); 4e: δ = 98 (s), 76 (s); in comparison: trimethylsilyl-N,N-dialkyl-1-alkynylamines: δ = 111 (s), 61 (s); 6b: δ = 76 (s), 60 (d); 6e: δ = 79 (s), 62 (d); in comparison N-methyl-N-phenyl-1-alkynylamine: δ = 84 (s), 56 (d).
28. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
29. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
30. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
31. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
32. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
33. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
34. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
35. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
36. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
37. Reviews: a) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1037-1064; b) N. E. Schore. Org. React. 1991, 40, 1-90; c) P. L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1988, p. 233; catalytic Pauson - Khand reactions: d) B. L. Pagenkof, T. Livinghouse, J. Am. Chem. Soc. 1996, 118, 2285-2286, e) B. Y. Lee, Y. K. Chung, N. Jeong, Y. Lee, S. H. Hwang, ibid. 1994, 116, 8793-8794; f) N. Jeong, S. H. Hwang, Y. Lee, Y. K. Chung, ibid. 1994, 116, 3159-3160; natural product synthesis: g) J. Tormo, A. Moyano, M. A. Pericàs, A. Riera, J. Org. Chem. 1997, 62, 4851-4856; h) C. Johnstone, W. J. Kerr, U. Lange, J. Chem. Soc. Chem. Commun. 1995, 457-458; i) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505-5506; j) C. Exon, P. Magnus, ibid. 1983, 105, 2477-2478.
38. a) A. R. Gordon, C. Johnstone, W. J. Kerr, Synlett 1995, 1083-1084;
39. b) N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, S.-E. Yoo, ibid. 1991, 204-206;
40. c) S. Shambayati, W. E. Crowe, S. L. Schreiber, Tetrahedron Lett. 1990, 31, 5289-5292.
41. W. A. Smit, S. L. Kireev, O. M. Nefedov, V. A. Tarasov, Tetrahedron Lett. 1989, 30, 4021-4024.
42. In all cases complete conversion of the starting material was observed. However the products were labile towards silica gel and tended to hydrolyze.
43. Details of the X-ray analysis (U. Bergsträsser, B. Witulski, Universität Kaiserslautern, 1997) will be published elsewhere.
44. We would like to express our thanks to Prof. Dr. L. Ernst (Technische Universität Braunschweig) for NOE and 2D-NMR measurements.
45. a) M. Costa, A. Mor, Tetrahedron Lett. 1995, 36, 2867-2870;
46. b) T. R. Hoye, J. A. Suriano, J. Am. Chem. Soc. 1993, 115, 1154-1156;
47. c) M. E. Krafft, R. H. Romero, I. L. Scott, J. Org. Chem. 1992, 57, 5277-5278;
48. d) F. Camps, J. M. Moretó, S. Ricart, J. M. Viñas, Angew. Chem. 1991, 103, 1540-1542; Angew. Chem. Int. Ed. Engl. 1991, 30, 1470-1472;
49. d) F. Camps, J. M. Moretó, S. Ricart, J. M. Viñas, Angew. Chem. 1991, 103, 1540-1542; Angew. Chem. Int. Ed. Engl. 1991, 30, 1470-1472;
50. e) M. E. Krafft, C. A. Juliano, I. L. Scott, C. Wright, M. D. McEachin, J. Am. Chem. Soc. 1991, 113, 1693-1703;
51. f) I. U. Khand, P. L. Pauson, J. Chem. Soc. Chem. Commun. 1974, 379.
52. a) N. Jeong, B. Y. Lee, S. M. Lee, Y. K. Chung, S.-G. Lee, Tetrahedron Lett. 1993, 34, 4023-4026;
53. b) P. Magnus, L. M. Prince, ibid. 1985, 26, 4851-4854.