[3+2] and [4+1] cycloaddition reactions of fischer alkoxy(alkenyl)carbene complexes with electronically neutral 1,3-dienes

Angewandte Chemie - International Edition

Volumn 42, Issue 2, 2003, Pages 231-233

  Barluenga, José ^a   López, Salomé ^a   Flórez, Josefa ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Asymmetric synthesis; Carbene ligands; Cycloaddition; Cyclopentenes diene ligands

Indexed keywords

ADDITION REACTIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TRANSITION METALS;

CYCLOADDITION;

ORGANIC COMPOUNDS;

ALKADIENE; CARBENOID; CYCLOPENTANE;

ARTICLE; COMPLEX FORMATION; CYCLOADDITION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037434138     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390087     Document Type: Article

References (39)

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29. With 1,3-dienes, the presence of this additive is required to inhibit polymerization.
30. For other [3+2] cycloadditions involving a three-carbon-atom synthon alkenylcarbene ligand, and other substrates, see for example: electron-deficient olefins: a) M. Hoffmann, H.-U. Reissig, Synlett 1995, 625; Enamines: b) J. Barluenga, M. Tomás, A. Ballesteros, J. Santamaría, C. Brillet, S. García-Granda, A. Piñera-Nicolás, J. T. Vázquez, J. Am. Chem. Soc. 1999, 121, 4516; Methyl ketone enolates: c) J. Barluenga, J. Alonso, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2000, 112, 2556; Angew. Chem. Int. Ed. 2000, 39, 2460; Imines: d) H. Kagoshima, T. Okamura, T. Akiyama, J. Am. Chem. Soc. 2001, 123, 7182; Alkynes: e) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell, J. Clardy, Organometallics 1994, 13, 102.
31. For other [3+2] cycloadditions involving a three-carbon-atom synthon alkenylcarbene ligand, and other substrates, see for example: electron-deficient olefins: a) M. Hoffmann, H.-U. Reissig, Synlett 1995, 625; Enamines: b) J. Barluenga, M. Tomás, A. Ballesteros, J. Santamaría, C. Brillet, S. García-Granda, A. Piñera-Nicolás, J. T. Vázquez, J. Am. Chem. Soc. 1999, 121, 4516; Methyl ketone enolates: c) J. Barluenga, J. Alonso, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2000, 112, 2556; Angew. Chem. Int. Ed. 2000, 39, 2460; Imines: d) H. Kagoshima, T. Okamura, T. Akiyama, J. Am. Chem. Soc. 2001, 123, 7182; Alkynes: e) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell, J. Clardy, Organometallics 1994, 13, 102.
32. For other [3+2] cycloadditions involving a three-carbon-atom synthon alkenylcarbene ligand, and other substrates, see for example: electron-deficient olefins: a) M. Hoffmann, H.-U. Reissig, Synlett 1995, 625; Enamines: b) J. Barluenga, M. Tomás, A. Ballesteros, J. Santamaría, C. Brillet, S. García-Granda, A. Piñera-Nicolás, J. T. Vázquez, J. Am. Chem. Soc. 1999, 121, 4516; Methyl ketone enolates: c) J. Barluenga, J. Alonso, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2000, 112, 2556; Angew. Chem. Int. Ed. 2000, 39, 2460; Imines: d) H. Kagoshima, T. Okamura, T. Akiyama, J. Am. Chem. Soc. 2001, 123, 7182; Alkynes: e) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell, J. Clardy, Organometallics 1994, 13, 102.
33. For other [3+2] cycloadditions involving a three-carbon-atom synthon alkenylcarbene ligand, and other substrates, see for example: electron-deficient olefins: a) M. Hoffmann, H.-U. Reissig, Synlett 1995, 625; Enamines: b) J. Barluenga, M. Tomás, A. Ballesteros, J. Santamaría, C. Brillet, S. García-Granda, A. Piñera-Nicolás, J. T. Vázquez, J. Am. Chem. Soc. 1999, 121, 4516; Methyl ketone enolates: c) J. Barluenga, J. Alonso, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2000, 112, 2556; Angew. Chem. Int. Ed. 2000, 39, 2460; Imines: d) H. Kagoshima, T. Okamura, T. Akiyama, J. Am. Chem. Soc. 2001, 123, 7182; Alkynes: e) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell, J. Clardy, Organometallics 1994, 13, 102.
34. For other [3+2] cycloadditions involving a three-carbon-atom synthon alkenylcarbene ligand, and other substrates, see for example: electron-deficient olefins: a) M. Hoffmann, H.-U. Reissig, Synlett 1995, 625; Enamines: b) J. Barluenga, M. Tomás, A. Ballesteros, J. Santamaría, C. Brillet, S. García-Granda, A. Piñera-Nicolás, J. T. Vázquez, J. Am. Chem. Soc. 1999, 121, 4516; Methyl ketone enolates: c) J. Barluenga, J. Alonso, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2000, 112, 2556; Angew. Chem. Int. Ed. 2000, 39, 2460; Imines: d) H. Kagoshima, T. Okamura, T. Akiyama, J. Am. Chem. Soc. 2001, 123, 7182; Alkynes: e) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell, J. Clardy, Organometallics 1994, 13, 102.
35. For other [3+2] cycloadditions involving a three-carbon-atom synthon alkenylcarbene ligand, and other substrates, see for example: electron-deficient olefins: a) M. Hoffmann, H.-U. Reissig, Synlett 1995, 625; Enamines: b) J. Barluenga, M. Tomás, A. Ballesteros, J. Santamaría, C. Brillet, S. García-Granda, A. Piñera-Nicolás, J. T. Vázquez, J. Am. Chem. Soc. 1999, 121, 4516; Methyl ketone enolates: c) J. Barluenga, J. Alonso, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2000, 112, 2556; Angew. Chem. Int. Ed. 2000, 39, 2460; Imines: d) H. Kagoshima, T. Okamura, T. Akiyama, J. Am. Chem. Soc. 2001, 123, 7182; Alkynes: e) W. D. Wulff, B. M. Bax, T. A. Brandvold, K. S. Chan, A. M. Gilbert, R. P. Hsung, J. Mitchell, J. Clardy, Organometallics 1994, 13, 102.
36. No asymmetric induction was observed in the cycloaddition reactions with the chiral menthyloxycarbene complex 1g.
37. The analogous treatment (10% BHT, THF, 120°C, 0.5 h) of complex la with 2b exclusively provided the [3+2] adduct 3d (75%).
38. For other [4+1] cycloadditions involving a one-carbon-atom synthon alkenylcarbene ligand, see: J. Barluenga, A. Ballesteros, J. Santamaría, M. Tomás, J. Organomet. Chem. 2002, 643-644, 363, and references therein.
39. For full details of the X-ray study, see: J. F. Van der Maelen Uría, S. García-Granda, S. López, Acta Crystallogr. Sect. E 2002, 58, m613.