Metal-catalyzed carbocyclization by intramolecular reaction of allylsilanes and allylstannanes with alkynes [4]

Journal of the American Chemical Society

Volumn 122, Issue 6, 2000, Pages 1221-1222

  Fernández Rivas, Carolina ^a   Méndez, María ^a   Echavarren, Antonio M ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; METAL; SILANE DERIVATIVE; TIN DERIVATIVE;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; LETTER; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0038420088     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993524b     Document Type: Letter

References (46)

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7. (d) For an alternative pathway see: Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 9728.
8. Reaction catalyzed by palladacyclopentadiene complexes: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636. (b) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. (c) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647. (d) Trost, B. M.; Yanai, M.; Hoogsteen, K. A. J. Am. Chem. Soc. 1993, 115, 5294. (e) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. (f) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (g) See also: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
9. Reaction catalyzed by palladacyclopentadiene complexes: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636. (b) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. (c) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647. (d) Trost, B. M.; Yanai, M.; Hoogsteen, K. A. J. Am. Chem. Soc. 1993, 115, 5294. (e) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. (f) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (g) See also: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
10. Reaction catalyzed by palladacyclopentadiene complexes: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636. (b) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. (c) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647. (d) Trost, B. M.; Yanai, M.; Hoogsteen, K. A. J. Am. Chem. Soc. 1993, 115, 5294. (e) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. (f) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (g) See also: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
11. Reaction catalyzed by palladacyclopentadiene complexes: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636. (b) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. (c) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647. (d) Trost, B. M.; Yanai, M.; Hoogsteen, K. A. J. Am. Chem. Soc. 1993, 115, 5294. (e) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. (f) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (g) See also: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
12. Reaction catalyzed by palladacyclopentadiene complexes: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636. (b) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. (c) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647. (d) Trost, B. M.; Yanai, M.; Hoogsteen, K. A. J. Am. Chem. Soc. 1993, 115, 5294. (e) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. (f) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (g) See also: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
13. Reaction catalyzed by palladacyclopentadiene complexes: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636. (b) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. (c) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647. (d) Trost, B. M.; Yanai, M.; Hoogsteen, K. A. J. Am. Chem. Soc. 1993, 115, 5294. (e) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. (f) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (g) See also: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
14. Reaction catalyzed by palladacyclopentadiene complexes: (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636. (b) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850. (c) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647. (d) Trost, B. M.; Yanai, M.; Hoogsteen, K. A. J. Am. Chem. Soc. 1993, 115, 5294. (e) Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085. (f) Trost, B. M.; Hashmi, A. S. K. J. Am. Chem. Soc. 1994, 116, 2183. (g) See also: Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
15. Reaction catalyzed by Ru complexes or Pt salts: (a) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049. (b) Blum, J.; Berr-Kraft, H.; Badrieh, Y. J. Org. Chem. 1995, 60, 5567. (c) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901. (d) Chatani, N.; Kataoka, K.; Sakurai, H.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
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38. The configuration of this compound has been determined by NOEDIFF or NOESY experiments. See the Supporting Information for details.
39. 1 was determined by the absence of the signal corresponding to the methylidene E-hydrogen (4.96 ppm) of 2. See the Supporting Information for details.
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42. 19b
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