Iron-Catalyzed Cross-Coupling Reactions: Efficient Synthesis of 2, 3-Allenol Derivatives

Angewandte Chemie - International Edition

Volumn 42, Issue 43, 2003, Pages 5355-5357

  Fürstner, Alois ^a   Méndez, María ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Alkynes; Allenes; Cross coupling; Epoxides; Iron

Indexed keywords

CATALYSIS; IRON COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DIASTEREOSELECTIVITY;

ALCOHOLS;

ALLENE DERIVATIVE; IRON;

ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHIRALITY; CROSS REACTION; ENANTIOMER; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0344012926     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352441     Document Type: Article

References (47)

1. For selected reviews, see: a) J. A. Marshall, Chem. Rev. 2000, 100, 3163-3185;
2. b) R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067-3125;
3. c) S. Ma, Acc. Chem. Res. 2003, 36, 701-712;
4. d) A. S. K. Hashmi, Angew. Chem. 2000, 112, 3737-3740; Angew. Chem. Int. Ed. 2000, 39, 3590-3593;
5. d) A. S. K. Hashmi, Angew. Chem. 2000, 112, 3737-3740; Angew. Chem. Int. Ed. 2000, 39, 3590-3593;
6. e) A. Hoffmann-Röder, N. Krause, Angew. Chem. 2002, 114, 3057-3059; Angew. Chem. Int. Ed. 2002, 41, 2933-2935;
7. e) A. Hoffmann-Röder, N. Krause, Angew. Chem. 2002, 114, 3057-3059; Angew. Chem. Int. Ed. 2002, 41, 2933-2935;
8. f) N. Krause, A. Hoffmann-Röder, J. Canisius, Synthesis 2002, 1759-1774;
9. g) H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, Wiley, New York, 1984, and references therein.
10. For a review, see: N. Krause, A. Hoffmann-Röder, in Modern Organocopper Chemistry (Ed.: N. Krause), Wiley-VCH, Weinheim, 2002, pp. 145-166, and references therein.
11. For a recent exception, see: Z. Wan, S. G. Nelson, J. Am. Chem. Soc. 2000, 122, 10 470-10 471.
12. For detailed studies on the effect of additives as well as for an indepth mechanistic discussion, see the following for leading references: a) A. Alexakis, I. Marek, P. Mangeney, J. F. Normant, J. Am. Chem. Soc. 1990, 112, 8042-8047;
13. b) A. Alexakis, I. Marek, P. Mangeney, J. F. Normant, Tetrahedron 1991, 47, 1677-1696.
14. C. Sahlberg, A. Claesson, J. Org. Chem. 1984, 49, 4120-4122.
15. a) C. J. Elsevier, P. Vermeer, J. Org. Chem. 1989, 54, 3726-3730;
16. b) H. Westmijze, I. Nap, J. Meijer, H. Kleijn, P. Vermeer, Recl. Trav. Chim. Pays-Bas 1983, 102, 154-157;
17. c) A. Claesson, L.-I. Olsson, J. Chem. Soc. Chem. Commun. 1979, 524-525.
18. a) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635; Angew. Chem. Int. Ed. 2002, 41, 609-612;
19. a) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635; Angew. Chem. Int. Ed. 2002, 41, 609-612;
20. b) A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863;
21. c) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
22. c) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323; Angew. Chem. Int. Ed. 2003, 42, 308-311.
23. a) D. J. Pasto, G. F. Hennion, R. H. Shults, A. Waterhouse, S.-K. Chou, J. Org. Chem. 1976, 41, 3496;
24. b) D. J. Pasto, S.-K. Chou, A. Waterhouse, R. H. Shults, G. F. Hennion, J. Org. Chem. 1978, 43, 1385-1388.
25. A. S. K. Hashmi, G. Szeimies, Chem. Ber. 1994, 127, 1075-1089.
26. For reports on the reaction of certain allylic substrates under iron catalysis, see: a) A. Yanagisawa, N. Nomura, H. Yamamoto, Tetrahedron 1994, 50, 6017-6028;
27. b) A. Yanagisawa, N. Nomura, H. Yamamoto, Synlett 1991, 513-514;
28. c) M. Nakamura, K. Matsuo, T. Inoue, E. Nakamura, Org. Lett. 2003, 5, 1373-1375;
29. d) M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 2000, 122, 978-979.
30. D. E. Frantz, R. Fassler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806-1807.
31. The enantiomerically enriched substrates used in this study were prepared by enantioselective oxidation of the corresponding enynes; see: Z.-X. Wang, G.-A. Cao, Y. Shi, J. Org. Chem. 1999, 64, 7646-7650.
32. 3].
33. Organocopper reagents show a certain tendency to undergo direct nucleophilic substitution of the epoxide, in particular if the reaction is carried out with only catalytic amounts of copper, see comments in reference [1f].
34. 3. [16c] All other compounds were assigned by analogy. A representative example is shown below.
35. a) P. Vermeer, J. Meijer, C. de Graaf, H. Schreurs, Recl. Trav. Chim. Pays-Bas 1974, 93, 46-47;
36. b) A. C. Oehlschlager, E. Czyzewska, Tetrahedron Lett. 1983, 24, 5587-5590;
37. c) J. A. Marshall, K. G. Pinney, J. Org. Chem. 1993, 58, 7180-7184;
38. d) C. Spino, S. Fréchette, Tetrahedron Lett. 2000, 41, 8033-8036;
39. e) C. R. Johnson, D. S. Dhanoa, J. Org. Chem. 1987, 52, 1885-1888;
40. f) A. Doutheau, A. Saba, J. Gore, G. Quash, Tetrahedron Lett. 1982, 23, 2461-2464;
41. g) P. R. Ortiz de Montellano, J. Chem. Soc. Chem. Commun. 1973, 709-710;
42. h) R. K. Dieter, L.E. Nice, Tetrahedron Lett. 1999, 40, 4293-4296;
43. i) F. Bertozzi, P. Crotti, F. Macchia, M. Pineschi, A. Arnold, B. L. Feringa, Tetrahedron Lett. 1999, 40, 4893-4896.
44. a) A similar rationale has been proposed for the formation of bromoallenes from propargyl alcohols and CuBr: N. Bernard, F. Chemea, J. F. Normant, Tetrahedron Lett. 1998, 39, 8837-8840;
45. b) for a review, see: A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307-1370.
46. For a recent application, see the following Communication in this issue: A. Fürstner, D. De Souza, L. Parra-Rapado, J. T. Jensen, Angew. Chem. 2003, 115, 5516-5518; Angew. Chem. Int. Ed. 2003, 42, 5358-5360.
47. For a recent application, see the following Communication in this issue: A. Fürstner, D. De Souza, L. Parra-Rapado, J. T. Jensen, Angew. Chem. 2003, 115, 5516-5518; Angew. Chem. Int. Ed. 2003, 42, 5358-5360.