Aldehyde addition and copper-mediated allylation of bicyclic alkoxytitanacyclopentenes and -pentadienes: New selectivities and an unusual reaction

Journal of the American Chemical Society

Volumn 121, Issue 6, 1999, Pages 1245-1255

  Urabe, Hirokazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKADIENE; COPPER; CYCLOPENTENE DERIVATIVE; DEUTERIUM; TITANIUM DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 0033576972     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982501e     Document Type: Article

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36. 18 which abstracts the nearby hydrogen of the titanacycle to give the radical intermediate 39. This radical intermediate collapses to give the new titanacycle 40 with hydrogen radical abstraction or radical disproportionation. matrix presented
37. Generation of α-oxy radicals by reduction of aldehydes and ketones with low-valent titanium reagents has been widely accepted as a step of the pinacol-type coupling reactions. For review, see: (a) Lenoir, D. Synthesis 1989, 883. (b) Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 563. (c) For latest reports, see: Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484. (d) Gansäuer, A. Synlett 1997, 457. (e) For other radical reactions induced by a low-valent titanium complex, see: RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986 and references therein.
38. Generation of α-oxy radicals by reduction of aldehydes and ketones with low-valent titanium reagents has been widely accepted as a step of the pinacol-type coupling reactions. For review, see: (a) Lenoir, D. Synthesis 1989, 883. (b) Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 563. (c) For latest reports, see: Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484. (d) Gansäuer, A. Synlett 1997, 457. (e) For other radical reactions induced by a low-valent titanium complex, see: RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986 and references therein.
39. Generation of α-oxy radicals by reduction of aldehydes and ketones with low-valent titanium reagents has been widely accepted as a step of the pinacol-type coupling reactions. For review, see: (a) Lenoir, D. Synthesis 1989, 883. (b) Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 563. (c) For latest reports, see: Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484. (d) Gansäuer, A. Synlett 1997, 457. (e) For other radical reactions induced by a low-valent titanium complex, see: RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986 and references therein.
40. Generation of α-oxy radicals by reduction of aldehydes and ketones with low-valent titanium reagents has been widely accepted as a step of the pinacol-type coupling reactions. For review, see: (a) Lenoir, D. Synthesis 1989, 883. (b) Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 563. (c) For latest reports, see: Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484. (d) Gansäuer, A. Synlett 1997, 457. (e) For other radical reactions induced by a low-valent titanium complex, see: RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986 and references therein.
41. Generation of α-oxy radicals by reduction of aldehydes and ketones with low-valent titanium reagents has been widely accepted as a step of the pinacol-type coupling reactions. For review, see: (a) Lenoir, D. Synthesis 1989, 883. (b) Robertson, G. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 563. (c) For latest reports, see: Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484. (d) Gansäuer, A. Synlett 1997, 457. (e) For other radical reactions induced by a low-valent titanium complex, see: RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986 and references therein.
42. Urabe, H.; Takeda, T.; Hideura, D.; Sato, F. J. Am. Chem. Soc. 1997, 119, 11295.
43. Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879 and references therein.
44. Titanium/copper transmetalation is quite rare (see ref 8a, p 89) and has been only documented in the reactions of alkyltitanium reagents. Arai, M.; Lipshutz, B. H.; Nakamura, E. Tetrahedron 1992, 48, 5709.
45. Copper-promoted reactions of group 4 transition metal intermediates have been centered on zirconium compounds. For reviews, see. (a) Wipf. P. Synthesis 1993, 537. (b) Wipf, P. Jahn, H. Tetrahedron 1996, 52, 12853. (c) Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277. (d) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639. (e) Kotora, M.; Xi, Z.; Takahashi, T. J. Synth. Org. Chem. Jpn. 1997, 55, 958.
46. Copper-promoted reactions of group 4 transition metal intermediates have been centered on zirconium compounds. For reviews, see. (a) Wipf. P. Synthesis 1993, 537. (b) Wipf, P. Jahn, H. Tetrahedron 1996, 52, 12853. (c) Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277. (d) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639. (e) Kotora, M.; Xi, Z.; Takahashi, T. J. Synth. Org. Chem. Jpn. 1997, 55, 958.
47. Copper-promoted reactions of group 4 transition metal intermediates have been centered on zirconium compounds. For reviews, see. (a) Wipf. P. Synthesis 1993, 537. (b) Wipf, P. Jahn, H. Tetrahedron 1996, 52, 12853. (c) Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277. (d) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639. (e) Kotora, M.; Xi, Z.; Takahashi, T. J. Synth. Org. Chem. Jpn. 1997, 55, 958.
48. Copper-promoted reactions of group 4 transition metal intermediates have been centered on zirconium compounds. For reviews, see. (a) Wipf. P. Synthesis 1993, 537. (b) Wipf, P. Jahn, H. Tetrahedron 1996, 52, 12853. (c) Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277. (d) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639. (e) Kotora, M.; Xi, Z.; Takahashi, T. J. Synth. Org. Chem. Jpn. 1997, 55, 958.
49. Copper-promoted reactions of group 4 transition metal intermediates have been centered on zirconium compounds. For reviews, see. (a) Wipf. P. Synthesis 1993, 537. (b) Wipf, P. Jahn, H. Tetrahedron 1996, 52, 12853. (c) Lipshutz, B. H. Acc. Chem. Res. 1997, 30, 277. (d) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639. (e) Kotora, M.; Xi, Z.; Takahashi, T. J. Synth. Org. Chem. Jpn. 1997, 55, 958.
50. 2-zirconacyclopentenes has been reported. Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun. 1995, 109.
51. 2-zirconacyclopentadienes in the presence of a copper salt has been reported. (a) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183. (b) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355.
52. 2-zirconacyclopentadienes in the presence of a copper salt has been reported. (a) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183. (b) Kotora, M.; Umeda, C.; Ishida, T.; Takahashi, T. Tetrahedron Lett. 1997, 38, 8355.