Pd(II)- and Pd(0)-cocatalyzed reactions of sulfonamides with MCPs

Organic Letters

Volumn 5, Issue 8, 2003, Pages 1225-1228

  Shi, Min ^a   Chen, Yu ^b   Xu, Bo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; PALLADIUM; SULFONAMIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 0141628939     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034146p     Document Type: Article

References (41)

1. (a) Synthesis of MCPs: Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 598.
2. (b) Carbocyclic Three-Membered Ring Compounds; de Meijere, A., Ed.; Houben-Weyl: Thieme, Stuttgart, 1996;
3. For a recent review, see: Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111.
4. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
5. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
6. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
7. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
8. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
9. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
10. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
11. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
12. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
13. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
14. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
15. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
16. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
17. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
18. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
19. For Pd(0)- or Pd(II)-catalyzed ring-opening reactions, please see: (a) Nüske, H.; Notlemeyer, M.; de Meijere, A. Angew. Chem., Int. Ed. 2001, 40, 3411. (b) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298. (c) Oh, B.-H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 6203. (d) Fournet, G.; Balme, G.; Goré, J. Tetrahedron 1988, 44, 5809. (e) Bräse, S.; de Meijere A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545. (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676. (g) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123. (h) Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999, 55, 8833. (i) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661. (j) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458. (k) Camacho, D. H.; Nakamura, I. ; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365. (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. (m) Binger, P.; B ch, H. M. Top. Curr. Chem. 1987, 135, 77. (n) Ohta, T.; Takaya, H. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol 5, pp 1185-1205. (o) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. (p) Zuber, R.; Carlens, G.; Haag, R.; de Meijere, A. Synlett 1996, 542.
20. (a) Trost, B. M.; Lee, D. C.; Rise, F. Tetrahedron Lett. 1989, 30, 651.
21. (b) Trost, B. M.; Li, Y. J. Am. Chem. Soc. 1996, 118, 6625.
22. (c) Trost, B. M.; Krische, M. J. Synlett 1998, 1.
23. 3, the precipitation of black Pd metal was observed during reaction.
24. 000 = 1240. Diffractometer: Rigaku AFC7R. Residuals: R, Rw: 0.0464, 0.0481.
25. Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
26. Lewis acid catalyzed ring-opening reaction of MCPs has been disclosed by our group: (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019. On the other hand, Kilburn reported Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropane with ketones and aldehydes: (c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 1615. (d) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilbum, J. D. Tetrahedron Lett. 2001, 42, 347. (e) Patient, L.; Berry, M. B.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1015.
27. Lewis acid catalyzed ring-opening reaction of MCPs has been disclosed by our group: (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019. On the other hand, Kilburn reported Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropane with ketones and aldehydes: (c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 1615. (d) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilbum, J. D. Tetrahedron Lett. 2001, 42, 347. (e) Patient, L.; Berry, M. B.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1015.
28. Lewis acid catalyzed ring-opening reaction of MCPs has been disclosed by our group: (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019. On the other hand, Kilburn reported Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropane with ketones and aldehydes: (c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 1615. (d) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilbum, J. D. Tetrahedron Lett. 2001, 42, 347. (e) Patient, L.; Berry, M. B.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1015.
29. Lewis acid catalyzed ring-opening reaction of MCPs has been disclosed by our group: (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019. On the other hand, Kilburn reported Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropane with ketones and aldehydes: (c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 1615. (d) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilbum, J. D. Tetrahedron Lett. 2001, 42, 347. (e) Patient, L.; Berry, M. B.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1015.
30. Lewis acid catalyzed ring-opening reaction of MCPs has been disclosed by our group: (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019. On the other hand, Kilburn reported Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropane with ketones and aldehydes: (c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 1615. (d) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilbum, J. D. Tetrahedron Lett. 2001, 42, 347. (e) Patient, L.; Berry, M. B.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1015.
31. (a) Sawamura, M.; Sudoh, M., Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309.
32. (b) Kamijo, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 3230.
33. (c) Ikeda, S.-i.; Mori, N.; Sato, Y. J. Am. Chem. Soc. 1997, 119, 4779.
34. 2 is the best Lewis acid for ring-opening reactions of MCPs 1 with alcoholic and aromatic amino nucleophiles.
35. 2 was prepared according to the literature: (a) Smith, J. K.; Bergbreiter, D. E.; Newcomb, M. J. Org. Chem. 1985, 50, 4549. (b) Inbar, S. ; Linschitz, H.; Cohen, S. G. J. Am. Chem. Soc. 1981, 103, 1048. Please also see ref 3j.
36. 2 was prepared according to the literature: (a) Smith, J. K.; Bergbreiter, D. E.; Newcomb, M. J. Org. Chem. 1985, 50, 4549. (b) Inbar, S. ; Linschitz, H.; Cohen, S. G. J. Am. Chem. Soc. 1981, 103, 1048. Please also see ref 3j.
37. (a) Prashad, M. J. Med. Chem. 1993, 36, 631.
38. (b) Stutz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320.
39. (c) Vedejs, E.; Gingras, M. J. Am. Chem. Soc. 1994, 116, 579.
40. (d) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron: Asymmetry 1997, 8, 3887.
41. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.