Regioselective Coupling Reaction of Allylic Barium Reagents with Epoxides

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 2, 1997, Pages 493-497

  Yasue, Katsutaka ^a   Yanagisawa, Akira ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008040604     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.493     Document Type: Article

References (45)

1. Reviews: a) G. Courtois and L. Miginiac, J. Organomet. Chem., 69, 1 (1974): b) R. A. Benkeser, Synthesis, 1971, 347. In general, γ-regioselectivity is obtained in the cross-coupling reaction of an epoxide with an allylic metal reagent, see: a) R. A. Benkeser, M. P. Siklosi, and E. C. Mozdzen, J. Am. Chem. Soc., 100, 2134 (1978); b) H. Felkin and C. Frajerman, Tetrahedron Lett., 1970, 1045: c) H. Felkin, C. Frajerman, and G. Roussi, Bull. Soc. Chim. Fr., 1970, 3704; d) C. Prevost, M. Andrac, F. Gaudemer, M. Gaudemer, B. Gross, L. Miginiac, and P. Miginiac, Bull. Soc. Chim. Fr., 1963, 1385; e) D. Abenhaim, E. Henry-Basch, and P. Freon. C. R. Acad. Sci. Paris, Ser. C, 267, 655 (1968).
2. Reviews: a) G. Courtois and L. Miginiac, J. Organomet. Chem., 69, 1 (1974): b) R. A. Benkeser, Synthesis, 1971, 347. In general, γ-regioselectivity is obtained in the cross-coupling reaction of an epoxide with an allylic metal reagent, see: a) R. A. Benkeser, M. P. Siklosi, and E. C. Mozdzen, J. Am. Chem. Soc., 100, 2134 (1978); b) H. Felkin and C. Frajerman, Tetrahedron Lett., 1970, 1045: c) H. Felkin, C. Frajerman, and G. Roussi, Bull. Soc. Chim. Fr., 1970, 3704; d) C. Prevost, M. Andrac, F. Gaudemer, M. Gaudemer, B. Gross, L. Miginiac, and P. Miginiac, Bull. Soc. Chim. Fr., 1963, 1385; e) D. Abenhaim, E. Henry-Basch, and P. Freon. C. R. Acad. Sci. Paris, Ser. C, 267, 655 (1968).
3. Reviews: a) G. Courtois and L. Miginiac, J. Organomet. Chem., 69, 1 (1974): b) R. A. Benkeser, Synthesis, 1971, 347. In general, γ-regioselectivity is obtained in the cross-coupling reaction of an epoxide with an allylic metal reagent, see: a) R. A. Benkeser, M. P. Siklosi, and E. C. Mozdzen, J. Am. Chem. Soc., 100, 2134 (1978); b) H. Felkin and C. Frajerman, Tetrahedron Lett., 1970, 1045: c) H. Felkin, C. Frajerman, and G. Roussi, Bull. Soc. Chim. Fr., 1970, 3704; d) C. Prevost, M. Andrac, F. Gaudemer, M. Gaudemer, B. Gross, L. Miginiac, and P. Miginiac, Bull. Soc. Chim. Fr., 1963, 1385; e) D. Abenhaim, E. Henry-Basch, and P. Freon. C. R. Acad. Sci. Paris, Ser. C, 267, 655 (1968).
4. Reviews: a) G. Courtois and L. Miginiac, J. Organomet. Chem., 69, 1 (1974): b) R. A. Benkeser, Synthesis, 1971, 347. In general, γ-regioselectivity is obtained in the cross-coupling reaction of an epoxide with an allylic metal reagent, see: a) R. A. Benkeser, M. P. Siklosi, and E. C. Mozdzen, J. Am. Chem. Soc., 100, 2134 (1978); b) H. Felkin and C. Frajerman, Tetrahedron Lett., 1970, 1045: c) H. Felkin, C. Frajerman, and G. Roussi, Bull. Soc. Chim. Fr., 1970, 3704; d) C. Prevost, M. Andrac, F. Gaudemer, M. Gaudemer, B. Gross, L. Miginiac, and P. Miginiac, Bull. Soc. Chim. Fr., 1963, 1385; e) D. Abenhaim, E. Henry-Basch, and P. Freon. C. R. Acad. Sci. Paris, Ser. C, 267, 655 (1968).
5. Reviews: a) G. Courtois and L. Miginiac, J. Organomet. Chem., 69, 1 (1974): b) R. A. Benkeser, Synthesis, 1971, 347. In general, γ-regioselectivity is obtained in the cross-coupling reaction of an epoxide with an allylic metal reagent, see: a) R. A. Benkeser, M. P. Siklosi, and E. C. Mozdzen, J. Am. Chem. Soc., 100, 2134 (1978); b) H. Felkin and C. Frajerman, Tetrahedron Lett., 1970, 1045: c) H. Felkin, C. Frajerman, and G. Roussi, Bull. Soc. Chim. Fr., 1970, 3704; d) C. Prevost, M. Andrac, F. Gaudemer, M. Gaudemer, B. Gross, L. Miginiac, and P. Miginiac, Bull. Soc. Chim. Fr., 1963, 1385; e) D. Abenhaim, E. Henry-Basch, and P. Freon. C. R. Acad. Sci. Paris, Ser. C, 267, 655 (1968).
6. Reviews: a) G. Courtois and L. Miginiac, J. Organomet. Chem., 69, 1 (1974): b) R. A. Benkeser, Synthesis, 1971, 347. In general, γ-regioselectivity is obtained in the cross-coupling reaction of an epoxide with an allylic metal reagent, see: a) R. A. Benkeser, M. P. Siklosi, and E. C. Mozdzen, J. Am. Chem. Soc., 100, 2134 (1978); b) H. Felkin and C. Frajerman, Tetrahedron Lett., 1970, 1045: c) H. Felkin, C. Frajerman, and G. Roussi, Bull. Soc. Chim. Fr., 1970, 3704; d) C. Prevost, M. Andrac, F. Gaudemer, M. Gaudemer, B. Gross, L. Miginiac, and P. Miginiac, Bull. Soc. Chim. Fr., 1963, 1385; e) D. Abenhaim, E. Henry-Basch, and P. Freon. C. R. Acad. Sci. Paris, Ser. C, 267, 655 (1968).
7. Reviews: a) G. Courtois and L. Miginiac, J. Organomet. Chem., 69, 1 (1974): b) R. A. Benkeser, Synthesis, 1971, 347. In general, γ-regioselectivity is obtained in the cross-coupling reaction of an epoxide with an allylic metal reagent, see: a) R. A. Benkeser, M. P. Siklosi, and E. C. Mozdzen, J. Am. Chem. Soc., 100, 2134 (1978); b) H. Felkin and C. Frajerman, Tetrahedron Lett., 1970, 1045: c) H. Felkin, C. Frajerman, and G. Roussi, Bull. Soc. Chim. Fr., 1970, 3704; d) C. Prevost, M. Andrac, F. Gaudemer, M. Gaudemer, B. Gross, L. Miginiac, and P. Miginiac, Bull. Soc. Chim. Fr., 1963, 1385; e) D. Abenhaim, E. Henry-Basch, and P. Freon. C. R. Acad. Sci. Paris, Ser. C, 267, 655 (1968).
8. G. Linstrumelle and co-workers reported α-selective cross-coupling reaction of allylic Grignard reagent with epoxides using copper catalyst: a) G. Linstrumelle, R. Lorne, and H. P. Dang, Tetrahedron Lett., 1978, 4069; b) C. Huynh, F. Derguini-Boumechal, and G. Linstrumelle, Tetrahedron Lett., 1979, 1503. See also: c) S. Takano, M. Yanase, M. Takahashi, and K. Ogasawara, Chem. Lett., 1987, 2017; d) H. Takayanagi, T. Shirasaka, and Y. Morita, Synthesis, 1991, 722.
9. G. Linstrumelle and co-workers reported α-selective cross-coupling reaction of allylic Grignard reagent with epoxides using copper catalyst: a) G. Linstrumelle, R. Lorne, and H. P. Dang, Tetrahedron Lett., 1978, 4069; b) C. Huynh, F. Derguini-Boumechal, and G. Linstrumelle, Tetrahedron Lett., 1979, 1503. See also: c) S. Takano, M. Yanase, M. Takahashi, and K. Ogasawara, Chem. Lett., 1987, 2017; d) H. Takayanagi, T. Shirasaka, and Y. Morita, Synthesis, 1991, 722.
10. G. Linstrumelle and co-workers reported α-selective cross-coupling reaction of allylic Grignard reagent with epoxides using copper catalyst: a) G. Linstrumelle, R. Lorne, and H. P. Dang, Tetrahedron Lett., 1978, 4069; b) C. Huynh, F. Derguini-Boumechal, and G. Linstrumelle, Tetrahedron Lett., 1979, 1503. See also: c) S. Takano, M. Yanase, M. Takahashi, and K. Ogasawara, Chem. Lett., 1987, 2017; d) H. Takayanagi, T. Shirasaka, and Y. Morita, Synthesis, 1991, 722.
11. G. Linstrumelle and co-workers reported α-selective cross-coupling reaction of allylic Grignard reagent with epoxides using copper catalyst: a) G. Linstrumelle, R. Lorne, and H. P. Dang, Tetrahedron Lett., 1978, 4069; b) C. Huynh, F. Derguini-Boumechal, and G. Linstrumelle, Tetrahedron Lett., 1979, 1503. See also: c) S. Takano, M. Yanase, M. Takahashi, and K. Ogasawara, Chem. Lett., 1987, 2017; d) H. Takayanagi, T. Shirasaka, and Y. Morita, Synthesis, 1991, 722.
12. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
13. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
14. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
15. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
16. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
17. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
18. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
19. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
20. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
21. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
22. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
23. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
24. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
25. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
26. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
27. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
28. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
29. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
30. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
31. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
32. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
33. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
34. Cross-coupling methods using allylic organometallics for preparing 1, 5-dienes: a) J. A. Katzenellenbogen and R. S. Lenox, J. Org. Chem., 38, 326 (1973); b) F. Derguini-Boumechal, R. Lorne, and G. Linstrumelle, Tetrahedron Lett., 1977, 1181; c) Y. Yamamoto and K. Maruyama, J. Am. Chem. Soc., 100, 6282 (1978); d) Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Am. Chem. Soc., 103, 1969 (1981); e) B. M. Trost and E. Keinan, Tetrahedron Lett., 21, 2595 (1980); f) J. Godschalx and J. K. Stille, Tetrahedron Lett., 21, 2599 (1980); g) Y Yamamoto, K. Maruyama, and K. Matsumoto, J. Chem. Soc., Chem. Commun., 1984, 548; h) A. Goliaszewski and J. Schwartz, Organometallics, 4, 417 (1985); i) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Chem. Commun., 1985, 1357; j) V. Calò, L. Lopez, and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301; k) K. Sekiya and E. Nakamura, Tetrahedron Lett., 29, 5155 (1988); l) T. Miyakoshi, H. Takazawa, and M. Hagimoto, Yukagaku, 39, 83 (1990); m) T. Miyakoshi, M. Hagimoto, and K. Narita, Yukagaku, 41, 207 (1992); n) S. Araki, T. Shimizu, S. Jin, and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1991, 824; o) A. Yanagisawa, N. Nomura, Y. Noritake, and H. Yamamoto, Synthesis, 1991, 1130; p) Y. Hatanaka, Y. Ebina, and T. Hiyama, J. Am. Chem. Soc., 113, 7075 (1991); q) T. Takeda, Y. Takagi, H. Takano, and T. Fujiwara. Tetrahedron Lett., 33, 5381 (1992); r) A. N. Kasatkin, Y. A. Prokopenko, A. M. Khabibov, and G. A. Tolstikov, Mendeleev Commun., 1993, 17; s) A. Yanagisawa, H. Hibino, N. Nomura, and H. Yamamoto, J. Am. Chem. Soc., 115, 5879 (1993); t) T. Fujii, T. Hirao, and Y. Ohshiro, Tetrahedron Lett., 34, 5601 (1993); u) A. Yanagisawa, N. Nomura, and H. Yamamoto, Tetrahedron, 50. 6017 (1994); v) A. Yanagisawa, N. Nomura, Y. Yamada, H. Hibino, and H. Yamamoto, Synlett, 1995, 841; w) T. Yokozawa, K. Furuhashi, and H. Natsume, Tetrahedron Lett., 36, 5243 (1995).
35. A preliminary result has been published: A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, K. Yasue, and H. Yamamoto, Bull. Chem. Soc. Jpn., 68, 1263 (1995).
36. Reaction with carbonyl compounds: a) A. Yanagisawa, S. Habaue, and H. Yamamoto, J. Am. Chem. Soc., 113, 5893 (1991); b) A. Yanagisawa, S. Habaue, K. Yasue, and H. Yamamoto, J. Am. Chem. Soc., 116, 6130 (1994).
37. Reaction with carbonyl compounds: a) A. Yanagisawa, S. Habaue, and H. Yamamoto, J. Am. Chem. Soc., 113, 5893 (1991); b) A. Yanagisawa, S. Habaue, K. Yasue, and H. Yamamoto, J. Am. Chem. Soc., 116, 6130 (1994).
38. Reactions with allylic halides: a) A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, and H. Yamamoto, J. Org. Chem., 57, 6386 (1992); b) E. J. Corey and W.-C. Shieh, Tetrahedron Lett., 33, 6435 (1992); c) E. J. Corey, M. C. Noe, and W.-C. Shieh, Tetrahedron Lett., 34, 5995 (1993); d) T. Tanimoto, Y. Tsujita, K. Hamano, H. Haruyama, T. Kinoshita, T. Hosoya, S. Kaneko, K. Tago, and H. Kogen, Tetrahedron Lett., 36, 6301 (1995); e) A. Yanagisawa, K. Yasue, and H. Yamamoto, Synlett, 1996, 842.
39. Reactions with allylic halides: a) A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, and H. Yamamoto, J. Org. Chem., 57, 6386 (1992); b) E. J. Corey and W.-C. Shieh, Tetrahedron Lett., 33, 6435 (1992); c) E. J. Corey, M. C. Noe, and W.-C. Shieh, Tetrahedron Lett., 34, 5995 (1993); d) T. Tanimoto, Y. Tsujita, K. Hamano, H. Haruyama, T. Kinoshita, T. Hosoya, S. Kaneko, K. Tago, and H. Kogen, Tetrahedron Lett., 36, 6301 (1995); e) A. Yanagisawa, K. Yasue, and H. Yamamoto, Synlett, 1996, 842.
40. Reactions with allylic halides: a) A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, and H. Yamamoto, J. Org. Chem., 57, 6386 (1992); b) E. J. Corey and W.-C. Shieh, Tetrahedron Lett., 33, 6435 (1992); c) E. J. Corey, M. C. Noe, and W.-C. Shieh, Tetrahedron Lett., 34, 5995 (1993); d) T. Tanimoto, Y. Tsujita, K. Hamano, H. Haruyama, T. Kinoshita, T. Hosoya, S. Kaneko, K. Tago, and H. Kogen, Tetrahedron Lett., 36, 6301 (1995); e) A. Yanagisawa, K. Yasue, and H. Yamamoto, Synlett, 1996, 842.
41. Reactions with allylic halides: a) A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, and H. Yamamoto, J. Org. Chem., 57, 6386 (1992); b) E. J. Corey and W.-C. Shieh, Tetrahedron Lett., 33, 6435 (1992); c) E. J. Corey, M. C. Noe, and W.-C. Shieh, Tetrahedron Lett., 34, 5995 (1993); d) T. Tanimoto, Y. Tsujita, K. Hamano, H. Haruyama, T. Kinoshita, T. Hosoya, S. Kaneko, K. Tago, and H. Kogen, Tetrahedron Lett., 36, 6301 (1995); e) A. Yanagisawa, K. Yasue, and H. Yamamoto, Synlett, 1996, 842.
42. Reactions with allylic halides: a) A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, and H. Yamamoto, J. Org. Chem., 57, 6386 (1992); b) E. J. Corey and W.-C. Shieh, Tetrahedron Lett., 33, 6435 (1992); c) E. J. Corey, M. C. Noe, and W.-C. Shieh, Tetrahedron Lett., 34, 5995 (1993); d) T. Tanimoto, Y. Tsujita, K. Hamano, H. Haruyama, T. Kinoshita, T. Hosoya, S. Kaneko, K. Tago, and H. Kogen, Tetrahedron Lett., 36, 6301 (1995); e) A. Yanagisawa, K. Yasue, and H. Yamamoto, Synlett, 1996, 842.
43. 5b)
44. The relatively low yield is due to the accompanying homo-coupling reaction.
45. V. J. Davisson, A. B. Woodside, T. R. Neal, K. E. Stremler, M. Muehlbacher, and C. D. Poulter, J. Org. Chem., 51, 4768 (1986).