Addition of hydrogen halides to alkylidenecyclopropanes: A highly efficient and stereoselective method for the preparation of homoallylic halides

Tetrahedron Letters

Volumn 44, Issue 5, 2003, Pages 985-987

  Siriwardana, Amal I ^a   Nakamura, Itaru ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

(1 BUTYLPENTYLIDENE)CYCLOPROPANE; (1 PHENYLBENZYLIDENE)CYCLOPROPANE; 1 BROMO 4 BUTYL 3 OCTENE; 1 CHLORO 3 UNDECENE; 4 BUTYL 1 CHLORO 3 OCTENE; 4 CHLORO 1,1 DIPHENYL 1 BUTENE; ALKANE DERIVATIVE; ALKENE DERIVATIVE; ALLYL COMPOUND; CYCLOPROPANE DERIVATIVE; HALIDE; HYDROBROMIC ACID; HYDROCHLORIC ACID; OCTANE; OCTYLIDENECYCLOPROPANE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; HIGH TEMPERATURE; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION TIME; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037467850     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02722-3     Document Type: Article

References (35)

1. Jung M.E., Fahr B.T., D'Amico D.C. J. Org. Chem. 63:1998;2982.
2. Biernacki W., Gdula A. Pol. J. Chem. 55:1981;849.
3. McCormick J.P., Barton D.L. J. Chem. Soc., Chem. Commun. 1975;303.
4. Julia M., Julia S., Guegan R. Bull. Soc. Chim. Fr. 1960;1072.
5. Biernacki W., Gdula A. Synthesis. 1:1979;37.
6. Readily available 5-bromo-2-methyl-2-pentene in Aldrich and Fluka Companies is very expensive, 11 300 yen/1 g in Aldrich.
7. Brandi A., Goti A. Chem. Rev. 98:1998;589 Carbocyclic Three-Membered Ring Compounds; Houben-Weyl; de Meijere, A., Ed.; Thieme: Stuttgart, 1996; Vol. E175.
8. Brandi A., Goti A. Chem. Rev. 98:1998;589 Carbocyclic Three-Membered Ring Compounds; Houben-Weyl; de Meijere, A., Ed.; Thieme: Stuttgart, 1996; Vol. E175.
9. Köster R., Arora S., Binger P. Liebigs Ann. Chem. 1973;1619.
10. Donskaya N.A., Shulishov E.V., Shabarov Yu.S. J. Org. Chem. USSR. 17:1982;1874.
11. The reaction was carried out in a well sealed pressure vial. Therefore, the reaction was conducted at 120°C even using ether as a solvent.
12. Utimoto K., Tamura M., Sisido K. Tetrahedron. 14:1973;1169.
13. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
14. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
15. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
16. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
17. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
18. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
19. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
20. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
21. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
22. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
23. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
24. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
25. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
26. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
27. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
28. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
29. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
30. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
31. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
32. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
33. For a review, (a) Nakamura, I.; Yamamoto. Y. Adv. Synth. Catal. 2002, 344, 111. For H-M addition, (b) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676; (c) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069; (d) Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059. For H-Nu addition, (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123; (f) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458; (g) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270; (h) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661; (i) Nakamura, I.; Siriwardana, A. I.; Saito, S.; Yamamoto Y. J. Org. Chem. 2002, 67, 3445; (j) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145. For M-M addition, (k) Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790; (l) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015. For R-X addition, (m) Fournet, G.; Balme G.; Goré, J. Tetrahedron 1988, 44, 5809; (n) Fournet, G.; Balme, G.; Barieux, J. J.; Goré, J. Tetrahedron 1988, 44, 5821; (o) Bräse, S.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2545; (p) Nüske, H.; Bräse, S.; Kozhushkov, S.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350. For [3+2] cycloaddition, (q) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780; (r) Binger, P.; Schuchardt, U. Chem. Ber. 1981, 114, 3313; (s) Trost, B. M. Angew. Chem. 1986, 98, 1; Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (t) Nakamura, I.; Oh, B.-H.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 1298.
34. For stable cyclopropylcarbinyl cation; (a) Klunder, A. J. H.; Zwanenburg, B. In Houben-Weyl, Methoden der Organischen Chemie; de Meijere, A., Ed.; Thieme: Stuttgart, German, 1997; Vol. E17c, p. 2419; (b) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p. 169, and references cited therein.
35. For stable cyclopropylcarbinyl cation; (a) Klunder, A. J. H.; Zwanenburg, B. In Houben-Weyl, Methoden der Organischen Chemie; de Meijere, A., Ed.; Thieme: Stuttgart, German, 1997; Vol. E17c, p. 2419; (b) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p. 169, and references cited therein.