Lewis acid-mediated cycloaddition of methylenecyclopropanes with aldehydes and imines: A facile access to indene, THF, and pyrrolidine Skeletons via Homoallylic Rearrangement Protocol

Organic Letters

Volumn 6, Issue 7, 2004, Pages 1175-1178

  Shi, Min ^a   Xu, Bo ^a   Huang, Jin Wen ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BROMINE; FLUORINE; IMINE; INDENE DERIVATIVE; LEWIS ACID; METHYLENECYCLOPROPANE; OXYGEN; PROLINE DERIVATIVE; PROPANE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 2342644677     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0498242     Document Type: Article

References (33)

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14. 4 see: Monti, H.; Rizzotto, D.; Leandri, G. Tetrahedron 1998, 54, 6725. For the cycloaddition of gem-dialkoxy-substituted MCPs with aldehydes and imines upon heating, see: (e) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553. (f) Yamago, S.; Yanagawa, M.; Nakamura, E. Chem. Lett. 1999, 879. For Ni(0)-catalyzed reactions of MCPs that occur by the proximal bond cleavage (pattern II), see: (g) Binger, P.; Schafer, B. Tetrahedron Lett. 1988, 29, 4539. (h) Binger, P.; Wedemann, P. Tetrahedron Lett. 1985, 26, 1045. (i) Noyori, R.; Odagi, T. J. Am. Chem. Soc. 1970, 92, 5780. (j) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
15. 4 see: Monti, H.; Rizzotto, D.; Leandri, G. Tetrahedron 1998, 54, 6725. For the cycloaddition of gem-dialkoxy-substituted MCPs with aldehydes and imines upon heating, see: (e) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553. (f) Yamago, S.; Yanagawa, M.; Nakamura, E. Chem. Lett. 1999, 879. For Ni(0)-catalyzed reactions of MCPs that occur by the proximal bond cleavage (pattern II), see: (g) Binger, P.; Schafer, B. Tetrahedron Lett. 1988, 29, 4539. (h) Binger, P.; Wedemann, P. Tetrahedron Lett. 1985, 26, 1045. (i) Noyori, R.; Odagi, T. J. Am. Chem. Soc. 1970, 92, 5780. (j) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
16. 4 see: Monti, H.; Rizzotto, D.; Leandri, G. Tetrahedron 1998, 54, 6725. For the cycloaddition of gem-dialkoxy-substituted MCPs with aldehydes and imines upon heating, see: (e) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553. (f) Yamago, S.; Yanagawa, M.; Nakamura, E. Chem. Lett. 1999, 879. For Ni(0)-catalyzed reactions of MCPs that occur by the proximal bond cleavage (pattern II), see: (g) Binger, P.; Schafer, B. Tetrahedron Lett. 1988, 29, 4539. (h) Binger, P.; Wedemann, P. Tetrahedron Lett. 1985, 26, 1045. (i) Noyori, R.; Odagi, T. J. Am. Chem. Soc. 1970, 92, 5780. (j) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
17. 4 see: Monti, H.; Rizzotto, D.; Leandri, G. Tetrahedron 1998, 54, 6725. For the cycloaddition of gem-dialkoxy-substituted MCPs with aldehydes and imines upon heating, see: (e) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553. (f) Yamago, S.; Yanagawa, M.; Nakamura, E. Chem. Lett. 1999, 879. For Ni(0)-catalyzed reactions of MCPs that occur by the proximal bond cleavage (pattern II), see: (g) Binger, P.; Schafer, B. Tetrahedron Lett. 1988, 29, 4539. (h) Binger, P.; Wedemann, P. Tetrahedron Lett. 1985, 26, 1045. (i) Noyori, R.; Odagi, T. J. Am. Chem. Soc. 1970, 92, 5780. (j) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
18. 4 see: Monti, H.; Rizzotto, D.; Leandri, G. Tetrahedron 1998, 54, 6725. For the cycloaddition of gem-dialkoxy-substituted MCPs with aldehydes and imines upon heating, see: (e) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553. (f) Yamago, S.; Yanagawa, M.; Nakamura, E. Chem. Lett. 1999, 879. For Ni(0)-catalyzed reactions of MCPs that occur by the proximal bond cleavage (pattern II), see: (g) Binger, P.; Schafer, B. Tetrahedron Lett. 1988, 29, 4539. (h) Binger, P.; Wedemann, P. Tetrahedron Lett. 1985, 26, 1045. (i) Noyori, R.; Odagi, T. J. Am. Chem. Soc. 1970, 92, 5780. (j) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
19. 4 see: Monti, H.; Rizzotto, D.; Leandri, G. Tetrahedron 1998, 54, 6725. For the cycloaddition of gem-dialkoxy-substituted MCPs with aldehydes and imines upon heating, see: (e) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553. (f) Yamago, S.; Yanagawa, M.; Nakamura, E. Chem. Lett. 1999, 879. For Ni(0)-catalyzed reactions of MCPs that occur by the proximal bond cleavage (pattern II), see: (g) Binger, P.; Schafer, B. Tetrahedron Lett. 1988, 29, 4539. (h) Binger, P.; Wedemann, P. Tetrahedron Lett. 1985, 26, 1045. (i) Noyori, R.; Odagi, T. J. Am. Chem. Soc. 1970, 92, 5780. (j) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
20. 4 see: Monti, H.; Rizzotto, D.; Leandri, G. Tetrahedron 1998, 54, 6725. For the cycloaddition of gem-dialkoxy-substituted MCPs with aldehydes and imines upon heating, see: (e) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553. (f) Yamago, S.; Yanagawa, M.; Nakamura, E. Chem. Lett. 1999, 879. For Ni(0)-catalyzed reactions of MCPs that occur by the proximal bond cleavage (pattern II), see: (g) Binger, P.; Schafer, B. Tetrahedron Lett. 1988, 29, 4539. (h) Binger, P.; Wedemann, P. Tetrahedron Lett. 1985, 26, 1045. (i) Noyori, R.; Odagi, T. J. Am. Chem. Soc. 1970, 92, 5780. (j) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
21. 4 see: Monti, H.; Rizzotto, D.; Leandri, G. Tetrahedron 1998, 54, 6725. For the cycloaddition of gem-dialkoxy-substituted MCPs with aldehydes and imines upon heating, see: (e) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553. (f) Yamago, S.; Yanagawa, M.; Nakamura, E. Chem. Lett. 1999, 879. For Ni(0)-catalyzed reactions of MCPs that occur by the proximal bond cleavage (pattern II), see: (g) Binger, P.; Schafer, B. Tetrahedron Lett. 1988, 29, 4539. (h) Binger, P.; Wedemann, P. Tetrahedron Lett. 1985, 26, 1045. (i) Noyori, R.; Odagi, T. J. Am. Chem. Soc. 1970, 92, 5780. (j) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
22. 4 see: Monti, H.; Rizzotto, D.; Leandri, G. Tetrahedron 1998, 54, 6725. For the cycloaddition of gem-dialkoxy-substituted MCPs with aldehydes and imines upon heating, see: (e) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553. (f) Yamago, S.; Yanagawa, M.; Nakamura, E. Chem. Lett. 1999, 879. For Ni(0)-catalyzed reactions of MCPs that occur by the proximal bond cleavage (pattern II), see: (g) Binger, P.; Schafer, B. Tetrahedron Lett. 1988, 29, 4539. (h) Binger, P.; Wedemann, P. Tetrahedron Lett. 1985, 26, 1045. (i) Noyori, R.; Odagi, T. J. Am. Chem. Soc. 1970, 92, 5780. (j) Nakamura, E.; Yamago, S. Acc. Chem. Res. 2002, 35, 867.
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24. The structures of 3d, 4b, and 5a were further determined by X-ray diffraction (Supporting Information).
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29. This type of phenyl migration has been reported. See: (a) Kirmse, W.; Günther, B. R. J. Am. Chem. Soc. 1978, 100, 3619. (b) Wiberg, K. B.; Ashe, A. J. J. Am. Chem. Soc. 1968, 90, 63. (c) Schleyer, P. R.; Majerski, Z. J. Am. Chem. Soc. 1970, 93, 665. (d) Majerski, Z.; Schleyer, P. R. J. Am. Chem. Soc. 1971, 93, 665.
30. This type of phenyl migration has been reported. See: (a) Kirmse, W.; Günther, B. R. J. Am. Chem. Soc. 1978, 100, 3619. (b) Wiberg, K. B.; Ashe, A. J. J. Am. Chem. Soc. 1968, 90, 63. (c) Schleyer, P. R.; Majerski, Z. J. Am. Chem. Soc. 1970, 93, 665. (d) Majerski, Z.; Schleyer, P. R. J. Am. Chem. Soc. 1971, 93, 665.
31. This type of phenyl migration has been reported. See: (a) Kirmse, W.; Günther, B. R. J. Am. Chem. Soc. 1978, 100, 3619. (b) Wiberg, K. B.; Ashe, A. J. J. Am. Chem. Soc. 1968, 90, 63. (c) Schleyer, P. R.; Majerski, Z. J. Am. Chem. Soc. 1970, 93, 665. (d) Majerski, Z.; Schleyer, P. R. J. Am. Chem. Soc. 1971, 93, 665.
32. For example, 4m, which shows strong anti-acetylcholine, anti-histamine, and anti-barium activities, has been synthesized by a much longer procedure. Ohki, S.; Hamaguchi, F.; Yanagi, T.; Yoshino, M. Chem. Pharm. Bull. 1966, 14, 187.
33. For other special transformations of MCPs 1 with aldehydes, see the Supporting Information.