Formal alkyne insertion into alkoxycarbene complexes: Simple access to enantiopure group 6 alkynyl(alkoxy)carbene complexes

Angewandte Chemie - International Edition

Volumn 44, Issue 31, 2005, Pages 4981-4983

  Barluenga, José ^a   De La Rúa, Ramón Bernardo ^a   De Sáa, Diana ^a   Ballesteros, Alfredo ^a   Tomás, Miguel ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Acetylides; Asymmetric synthesis; Carbene complexes; Cycloaddition; Rearrangements

Indexed keywords

ADDITION REACTIONS; HYDROCARBONS; POLYMERS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

ACETYLIDES; ASYMMETRIC SYNTHESIS; CARBENE COMPLEXES; CYCLOADDITION; REARRANGEMENTS;

COMPLEXATION;

EID: 23744463209     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501400     Document Type: Article

References (40)

1. a) E. O. Fischer, A. Maäsbol, Angew. Chem. 1964, 76, 645;
2. b) F. Z. Dörwal, Metal Carbenes in Organic Synthesis, Wiley-VCH, New York, 1999;
3. c) A. de Meijere, H. Schirmer, M. Duetsch, Angew. Chem. 2000, 112, 4124;
4. Angew. Chem. Int. Ed. 2000, 39, 3964.
5. a) W. D. Wulff, Organometallics 1998, 17, 3116;
6. b) K. H. Dötz, P. Tomuschat, Chem. Soc. Rev. 1999, 28, 187.
7. For recent papers, see : a) H. Kagoshima, T. Okamura, T. Akiyama, J. Am. Chem. Soc. 2001, 123, 7182;
8. b) J. Barluenga, S. K. Nandy, Y. R. S. Laxmi, J. R. Suárez, I. Merino, J. Flórez, S. García-Granda, J. Montejo-Bernardo, Chem. Eur. J. 2003, 9, 5725.
9. Aldol: a) T. S. Powers, Y. Shi, K. J. Wilson, W. D. Wulff, A. L. Rheingold, J. Org. Chem. 1994, 59, 6882;
10. for [4+2] cycloaddition, see: b) T. S. Powers, W. Jiang, J. Su, W. D. Wulff, B. E. Waltermire, A. L. Rheingold, J. Am. Chem. Soc. 1997, 119, 6438;
11. for Michael addition to nitroolefins, see: c) E. Licandro, S. Maiorana, L. Capella, R. Manzotti, A. Papagni, B. Vandoni, A. Albinati, S. H. Chuang, J.-R. Hwu, Organometallics 2001, 20, 485.
12. The methoxy-amine exchange reaction has occasionally served in the preparation of amino carbenes C (X* = (S)-methoxymethylpyrrolidines): A. Rahm, A. L. Rheingold, W. D. Wulff, Tetrahedron 2000, 56, 4951.
13. J. Barluenga, A. Ballesteros, R. Bernardo de la Rúa, J. Santamaría, E. Rubio, M. Tomás, J. Am. Chem. Soc. 2003, 125, 1834.
14. a) T. Shimizu, D. Miyasaka, N. Kamigata, Org. Lett. 2000, 2, 1923;
15. b) further chemical characterization of 2 can be undertaken by oxidation with pyridine oxide to 1,3-diphenyl-1-propynone.
16. A. Padwa, D. J. Austin, Y. Gareau, J. M. Kassir, S. L. Xu, J. Am. Chem. Soc. 1993, 115, 2637.
17. C. P. Casey, S. Kraft, D. R. Powell, J. Am. Chem. Soc. 2003, 125, 2584.
18. a) C. P. Casey, T. L. Dzwiniel, S. Kraft, I. A. Guzei, Organometallics 2003, 22, 3915;
19. b) C. P. Casey, T. L. Dzwiniel, Organometallics 2003, 22, 5285;
20. c) Y Ortin, A. Sournia-Saquet, N. Lugan, R. Mathieu, Chem. Commun. 2003, 1060.
21. The formation of diynyl(amino)carbene complexes by copper-catalyzed coupling of pentacarbonyl[ethynyl(amino)carbene]-tungsten(0) with bromoalkynes is known: C. Hartbaum, H. Fischer, Chem. Ber. 1997, 130, 1063.
22. a) The pentacarbonyl[phenylethynyl(ethoxy)carbene]molybdenum(0) complex has been used for kinetic studies, but details on its preparation and spectral data are not given: R. Pipoh, R. van Eldik, G. Henkel, Organometallics 1993, 12, 2236;
23. b) Carbonylcyclopentadienyl [methoxy(4-methylphenyl)ethynylcarbene] nitrosylmolybdenum has been obtained in 12% yield: K. H. Dötz, C. Christoffers, J. Christoffers, D. Böttcher, M. Nieger, S. Kotila, Chem. Ber. 1995, 128, 645.
24. [5]
25. a) For [4+2] cycloaddition of chiral acetylenic diesters, see: R. N. Buckle, D. J. Burnell, Tetrahedron 1999, 55, 14829;
26. b) for [2+2] cycloaddition of chiral acetylenic acyl sultam, see : K. Villeneuve, W. Tam, Angew. Chem. 2004, 116, 620;
27. Angew. Chem. Int. Ed. 2004, 43, 610.
28. For leading papers on asymmetric, catalyzed reactions involving alkynes, see: a) E. J. Corey, T. W. Lee, Tetrahedron Lett. 1997, 38, 5755;
29. b) K. Ishihara, S. Kondo, H. Kurihara, H. Yamamoto, S. Ohashi, S. Inagaki, J. Org. Chem. 1997, 62, 3026;
30. c) R. Shintani, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 10778;
31. R. Shintani, G. C. Fu, Angew. Chem. 2003, 115, 4216;
32. Angew. Chem. Int. Ed. 2003, 42, 4082.
33. The model reaction with achiral carbenes was reported: J. Barluenga, M. Tomás, J. A. López-Pelegrín, E. Rubio, Tetrahedron Lett. 1997, 38, 3981.
34. CCDC-268 919 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.
35. J. Barluenga, J. M. Monserrat, J. Flórez, S. García-Granda, E. Martin, Chem. Eur. J. 1995, 1, 236.
36. A reviewer pointed out that the cyclization of 13 into 12 could be seen, not only as an intramolecular Michael-type addition, but alternatively as an electrocyclization reaction, a) for pseudopericyclic cyclizations of (Z)-1,2,4,6-heptatetraene derivatives, see: J. Rodríguez-Otero, E. M. Cabaleiro-Lago, Chem. Eur. J. 2003, 9, 1837;
37. b) for torquoselectivity in electrocyclic reactions of 1-aza-1,3,5-trienes, see: M. J. Walker, B. N. Hietbrink, B. E. Thomas, IV, K. Nakamura, E. A. Kallel, K. N. Houk, J. Org. Chem. 2001, 66, 6669;
38. c) for a preliminary communication on torquoselectivity in electrocyclic reactions of (Z)-1,2,4,6-heptatetraenes, see: B. N. Hietbrink, C. A. Merlic, K. N. Houk, Abstract of Papers, 221st ACS National Meeting, San Diego (CA), 2001, ORGN-354.
39. This demetalation procedure will be optimized and the details publish elsewhere.
40. For efficient access through 1,4-nucleophilic addition of ketene silyl acetals to chiral pyridinium salts, see: S. Yamada, C. Morita, J. Am. Chem. Soc. 2002, 124, 8184.