Efficient and stereospecific construction of asymmetric quaternary carbons via γ-alkyl-γ,δ-epoxy acrylates

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3775-3778

  Ishibashi, Naoki ^a   Miyazawa, Masahiro ^a   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; CARBON;

ALKYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0032575149     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00614-5     Document Type: Article

References (23)

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2. 1 S. F. Martin, Tetrahedron, 1980, 36, 419-460; K. Fuji, Chem. Rev., 1993, 93, 2037-2066; D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292-2303; N. Watanabe, Y. Ohtake, S. Hashimoto, M. Shiro, and S. Ikegami, Tetrahedron Lett., 1995, 36, 1491-1494; T. Takemoto, M. Sodeoka, and M. Shibasaki, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 36th, 220-227 (1994); Y. Kataoka, I. Makihira, H. Akiyama, and K. Tani, Tetrahedron Lett., 1995, 36, 6495-6498; T. Fosaka, T. Ueda, Y, Fujiwara, Y. Miki, O. Iire, T, Omodani, and K. Shishido, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 37th, 379-384 (1995); T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki, J. Am. Chem. Soc., 1995, 117, 10757-10758; Y. Yamamoto, S. Hara, and A, Suzuki, Synlett, 1996, 883-884; C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, and A. Linden, J. Org. Chem., 1997, 62, 2070-2079; S. E. Denmark and L. R. Marcin, ibid., 1997, 62, 1675-1686; J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963-1966; M. Murakata, T. Jono, Y. Mizuno, and O. Hoshino, J. Am. Chem. Soc., 1997, 119, 11713-11714.
3. 1 S. F. Martin, Tetrahedron, 1980, 36, 419-460; K. Fuji, Chem. Rev., 1993, 93, 2037-2066; D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292-2303; N. Watanabe, Y. Ohtake, S. Hashimoto, M. Shiro, and S. Ikegami, Tetrahedron Lett., 1995, 36, 1491-1494; T. Takemoto, M. Sodeoka, and M. Shibasaki, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 36th, 220-227 (1994); Y. Kataoka, I. Makihira, H. Akiyama, and K. Tani, Tetrahedron Lett., 1995, 36, 6495-6498; T. Fosaka, T. Ueda, Y, Fujiwara, Y. Miki, O. Iire, T, Omodani, and K. Shishido, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 37th, 379-384 (1995); T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki, J. Am. Chem. Soc., 1995, 117, 10757-10758; Y. Yamamoto, S. Hara, and A, Suzuki, Synlett, 1996, 883-884; C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, and A. Linden, J. Org. Chem., 1997, 62, 2070-2079; S. E. Denmark and L. R. Marcin, ibid., 1997, 62, 1675-1686; J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963-1966; M. Murakata, T. Jono, Y. Mizuno, and O. Hoshino, J. Am. Chem. Soc., 1997, 119, 11713-11714.
4. 1 S. F. Martin, Tetrahedron, 1980, 36, 419-460; K. Fuji, Chem. Rev., 1993, 93, 2037-2066; D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292-2303; N. Watanabe, Y. Ohtake, S. Hashimoto, M. Shiro, and S. Ikegami, Tetrahedron Lett., 1995, 36, 1491-1494; T. Takemoto, M. Sodeoka, and M. Shibasaki, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 36th, 220-227 (1994); Y. Kataoka, I. Makihira, H. Akiyama, and K. Tani, Tetrahedron Lett., 1995, 36, 6495-6498; T. Fosaka, T. Ueda, Y, Fujiwara, Y. Miki, O. Iire, T, Omodani, and K. Shishido, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 37th, 379-384 (1995); T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki, J. Am. Chem. Soc., 1995, 117, 10757-10758; Y. Yamamoto, S. Hara, and A, Suzuki, Synlett, 1996, 883-884; C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, and A. Linden, J. Org. Chem., 1997, 62, 2070-2079; S. E. Denmark and L. R. Marcin, ibid., 1997, 62, 1675-1686; J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963-1966; M. Murakata, T. Jono, Y. Mizuno, and O. Hoshino, J. Am. Chem. Soc., 1997, 119, 11713-11714.
5. 1 S. F. Martin, Tetrahedron, 1980, 36, 419-460; K. Fuji, Chem. Rev., 1993, 93, 2037-2066; D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292-2303; N. Watanabe, Y. Ohtake, S. Hashimoto, M. Shiro, and S. Ikegami, Tetrahedron Lett., 1995, 36, 1491-1494; T. Takemoto, M. Sodeoka, and M. Shibasaki, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 36th, 220-227 (1994); Y. Kataoka, I. Makihira, H. Akiyama, and K. Tani, Tetrahedron Lett., 1995, 36, 6495-6498; T. Fosaka, T. Ueda, Y, Fujiwara, Y. Miki, O. Iire, T, Omodani, and K. Shishido, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 37th, 379-384 (1995); T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki, J. Am. Chem. Soc., 1995, 117, 10757-10758; Y. Yamamoto, S. Hara, and A, Suzuki, Synlett, 1996, 883-884; C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, and A. Linden, J. Org. Chem., 1997, 62, 2070-2079; S. E. Denmark and L. R. Marcin, ibid., 1997, 62, 1675-1686; J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963-1966; M. Murakata, T. Jono, Y. Mizuno, and O. Hoshino, J. Am. Chem. Soc., 1997, 119, 11713-11714.
6. 1 S. F. Martin, Tetrahedron, 1980, 36, 419-460; K. Fuji, Chem. Rev., 1993, 93, 2037-2066; D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292-2303; N. Watanabe, Y. Ohtake, S. Hashimoto, M. Shiro, and S. Ikegami, Tetrahedron Lett., 1995, 36, 1491-1494; T. Takemoto, M. Sodeoka, and M. Shibasaki, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 36th, 220-227 (1994); Y. Kataoka, I. Makihira, H. Akiyama, and K. Tani, Tetrahedron Lett., 1995, 36, 6495-6498; T. Fosaka, T. Ueda, Y, Fujiwara, Y. Miki, O. Iire, T, Omodani, and K. Shishido, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 37th, 379-384 (1995); T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki, J. Am. Chem. Soc., 1995, 117, 10757-10758; Y. Yamamoto, S. Hara, and A, Suzuki, Synlett, 1996, 883-884; C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, and A. Linden, J. Org. Chem., 1997, 62, 2070-2079; S. E. Denmark and L. R. Marcin, ibid., 1997, 62, 1675-1686; J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963-1966; M. Murakata, T. Jono, Y. Mizuno, and O. Hoshino, J. Am. Chem. Soc., 1997, 119, 11713-11714.
7. 1 S. F. Martin, Tetrahedron, 1980, 36, 419-460; K. Fuji, Chem. Rev., 1993, 93, 2037-2066; D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292-2303; N. Watanabe, Y. Ohtake, S. Hashimoto, M. Shiro, and S. Ikegami, Tetrahedron Lett., 1995, 36, 1491-1494; T. Takemoto, M. Sodeoka, and M. Shibasaki, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 36th, 220-227 (1994); Y. Kataoka, I. Makihira, H. Akiyama, and K. Tani, Tetrahedron Lett., 1995, 36, 6495-6498; T. Fosaka, T. Ueda, Y, Fujiwara, Y. Miki, O. Iire, T, Omodani, and K. Shishido, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 37th, 379-384 (1995); T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki, J. Am. Chem. Soc., 1995, 117, 10757-10758; Y. Yamamoto, S. Hara, and A, Suzuki, Synlett, 1996, 883-884; C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, and A. Linden, J. Org. Chem., 1997, 62, 2070-2079; S. E. Denmark and L. R. Marcin, ibid., 1997, 62, 1675-1686; J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963-1966; M. Murakata, T. Jono, Y. Mizuno, and O. Hoshino, J. Am. Chem. Soc., 1997, 119, 11713-11714.
8. 1 S. F. Martin, Tetrahedron, 1980, 36, 419-460; K. Fuji, Chem. Rev., 1993, 93, 2037-2066; D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292-2303; N. Watanabe, Y. Ohtake, S. Hashimoto, M. Shiro, and S. Ikegami, Tetrahedron Lett., 1995, 36, 1491-1494; T. Takemoto, M. Sodeoka, and M. Shibasaki, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 36th, 220-227 (1994); Y. Kataoka, I. Makihira, H. Akiyama, and K. Tani, Tetrahedron Lett., 1995, 36, 6495-6498; T. Fosaka, T. Ueda, Y, Fujiwara, Y. Miki, O. Iire, T, Omodani, and K. Shishido, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 37th, 379-384 (1995); T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki, J. Am. Chem. Soc., 1995, 117, 10757-10758; Y. Yamamoto, S. Hara, and A, Suzuki, Synlett, 1996, 883-884; C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, and A. Linden, J. Org. Chem., 1997, 62, 2070-2079; S. E. Denmark and L. R. Marcin, ibid., 1997, 62, 1675-1686; J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963-1966; M. Murakata, T. Jono, Y. Mizuno, and O. Hoshino, J. Am. Chem. Soc., 1997, 119, 11713-11714.
9. 1 S. F. Martin, Tetrahedron, 1980, 36, 419-460; K. Fuji, Chem. Rev., 1993, 93, 2037-2066; D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292-2303; N. Watanabe, Y. Ohtake, S. Hashimoto, M. Shiro, and S. Ikegami, Tetrahedron Lett., 1995, 36, 1491-1494; T. Takemoto, M. Sodeoka, and M. Shibasaki, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 36th, 220-227 (1994); Y. Kataoka, I. Makihira, H. Akiyama, and K. Tani, Tetrahedron Lett., 1995, 36, 6495-6498; T. Fosaka, T. Ueda, Y, Fujiwara, Y. Miki, O. Iire, T, Omodani, and K. Shishido, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 37th, 379-384 (1995); T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki, J. Am. Chem. Soc., 1995, 117, 10757-10758; Y. Yamamoto, S. Hara, and A, Suzuki, Synlett, 1996, 883-884; C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, and A. Linden, J. Org. Chem., 1997, 62, 2070-2079; S. E. Denmark and L. R. Marcin, ibid., 1997, 62, 1675-1686; J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963-1966; M. Murakata, T. Jono, Y. Mizuno, and O. Hoshino, J. Am. Chem. Soc., 1997, 119, 11713-11714.
10. 1 S. F. Martin, Tetrahedron, 1980, 36, 419-460; K. Fuji, Chem. Rev., 1993, 93, 2037-2066; D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292-2303; N. Watanabe, Y. Ohtake, S. Hashimoto, M. Shiro, and S. Ikegami, Tetrahedron Lett., 1995, 36, 1491-1494; T. Takemoto, M. Sodeoka, and M. Shibasaki, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 36th, 220-227 (1994); Y. Kataoka, I. Makihira, H. Akiyama, and K. Tani, Tetrahedron Lett., 1995, 36, 6495-6498; T. Fosaka, T. Ueda, Y, Fujiwara, Y. Miki, O. Iire, T, Omodani, and K. Shishido, Tennen Yuki Kagoubutu Toronkai Koen Yoshisyu, 37th, 379-384 (1995); T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki, J. Am. Chem. Soc., 1995, 117, 10757-10758; Y. Yamamoto, S. Hara, and A, Suzuki, Synlett, 1996, 883-884; C. Palomo, J. M. Aizpurua, J. M. García, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, J. Server-Carrió, and A. Linden, J. Org. Chem., 1997, 62, 2070-2079; S. E. Denmark and L. R. Marcin, ibid., 1997, 62, 1675-1686; J. C. F. Alves, A. B. C. Simas, P. R. R. Costa, and J. d'Angelo, Tetrahedron: Asymmetry, 1997, 8, 1963-1966; M. Murakata, T. Jono, Y. Mizuno, and O. Hoshino, J. Am. Chem. Soc., 1997, 119, 11713-11714.
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17. 4 M. Miyashita, K. Yoshihara, K. Kawamine, M. Hoshino, and H. Irie, Tetrahedron Lett., 1993, 34, 6285-6288; T. Shiratani, K. Kimura, K. Yoshihara, S. Hatakeyama, H. Irie, and M. Miyashita, J. Chem. Soc. Chem. Commun., 1996, 21-22; M. Miyashita, T. Shiratani, K. Kawamine, S. Hatakeyama, and H. Irie, ibid., 1996, 1027-1028; M. Miyazawa, S. Oonuma, K. Maruyama, and M. Miyashita, Chem. Lett., 1997, 1191-1192; M. Miyazawa, S. Oonuma, K. Maruyama, and M. Miyashita, ibid., 1997, 1193-1194.
18. 4 M. Miyashita, K. Yoshihara, K. Kawamine, M. Hoshino, and H. Irie, Tetrahedron Lett., 1993, 34, 6285-6288; T. Shiratani, K. Kimura, K. Yoshihara, S. Hatakeyama, H. Irie, and M. Miyashita, J. Chem. Soc. Chem. Commun., 1996, 21-22; M. Miyashita, T. Shiratani, K. Kawamine, S. Hatakeyama, and H. Irie, ibid., 1996, 1027-1028; M. Miyazawa, S. Oonuma, K. Maruyama, and M. Miyashita, Chem. Lett., 1997, 1191-1192; M. Miyazawa, S. Oonuma, K. Maruyama, and M. Miyashita, ibid., 1997, 1193-1194.
19. 4 M. Miyashita, K. Yoshihara, K. Kawamine, M. Hoshino, and H. Irie, Tetrahedron Lett., 1993, 34, 6285-6288; T. Shiratani, K. Kimura, K. Yoshihara, S. Hatakeyama, H. Irie, and M. Miyashita, J. Chem. Soc. Chem. Commun., 1996, 21-22; M. Miyashita, T. Shiratani, K. Kawamine, S. Hatakeyama, and H. Irie, ibid., 1996, 1027-1028; M. Miyazawa, S. Oonuma, K. Maruyama, and M. Miyashita, Chem. Lett., 1997, 1191-1192; M. Miyazawa, S. Oonuma, K. Maruyama, and M. Miyashita, ibid., 1997, 1193-1194.
20. 4 M. Miyashita, K. Yoshihara, K. Kawamine, M. Hoshino, and H. Irie, Tetrahedron Lett., 1993, 34, 6285-6288; T. Shiratani, K. Kimura, K. Yoshihara, S. Hatakeyama, H. Irie, and M. Miyashita, J. Chem. Soc. Chem. Commun., 1996, 21-22; M. Miyashita, T. Shiratani, K. Kawamine, S. Hatakeyama, and H. Irie, ibid., 1996, 1027-1028; M. Miyazawa, S. Oonuma, K. Maruyama, and M. Miyashita, Chem. Lett., 1997, 1191-1192; M. Miyazawa, S. Oonuma, K. Maruyama, and M. Miyashita, ibid., 1997, 1193-1194.
21. N 2' product (8%) and a rearranged 5-keto compound (7%).
22. -1.
23. -1.