Asymmetric γ-Selective Pentadienylation of Aldehydes Catalyzed by BINAP·Ag(I) Complex

Synlett

Volumn 1997, Issue 8, 1997, Pages 933-934

  Yanagisawa, Akira ^a   Nakatsuka, Yoshinari ^a   Nakashima, Hiroshi ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003183775     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-945     Document Type: Article

References (28)

1. Reviews: (a) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (b) Yasuda, H.; Nakamura, A. J. Organomet. Chem. 1985, 285, 15.
2. Reviews: (a) Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. (b) Yasuda, H.; Nakamura, A. J. Organomet. Chem. 1985, 285, 15.
3. 2: (g) Lin, S.-H.; Yang, Y.-J.; Liu, R.-S. J. Chem. Soc., Chem. Commun. 1991, 1004. (h) Lin, S.-H.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. Organometallics 1993, 12, 2591.
4. 2: (g) Lin, S.-H.; Yang, Y.-J.; Liu, R.-S. J. Chem. Soc., Chem. Commun. 1991, 1004. (h) Lin, S.-H.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. Organometallics 1993, 12, 2591.
5. 2: (g) Lin, S.-H.; Yang, Y.-J.; Liu, R.-S. J. Chem. Soc., Chem. Commun. 1991, 1004. (h) Lin, S.-H.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. Organometallics 1993, 12, 2591.
6. 2: (g) Lin, S.-H.; Yang, Y.-J.; Liu, R.-S. J. Chem. Soc., Chem. Commun. 1991, 1004. (h) Lin, S.-H.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. Organometallics 1993, 12, 2591.
7. 2: (g) Lin, S.-H.; Yang, Y.-J.; Liu, R.-S. J. Chem. Soc., Chem. Commun. 1991, 1004. (h) Lin, S.-H.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. Organometallics 1993, 12, 2591.
8. 2: (g) Lin, S.-H.; Yang, Y.-J.; Liu, R.-S. J. Chem. Soc., Chem. Commun. 1991, 1004. (h) Lin, S.-H.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. Organometallics 1993, 12, 2591.
9. 2: (g) Lin, S.-H.; Yang, Y.-J.; Liu, R.-S. J. Chem. Soc., Chem. Commun. 1991, 1004. (h) Lin, S.-H.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. Organometallics 1993, 12, 2591.
10. 2: (g) Lin, S.-H.; Yang, Y.-J.; Liu, R.-S. J. Chem. Soc., Chem. Commun. 1991, 1004. (h) Lin, S.-H.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. Organometallics 1993, 12, 2591.
11. Pentadienylzincs: (a) Gérard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924. (b) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101. (c) Kang, S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun. 1996, 26, 1493. (d) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667. Pentadienylmagnesiums: (e) Yasuda, H.; Yamauchi, M.; Nakamura, A.; Sei, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1089. Pentadienylberylliums: ref. 3b. Pentadienylboranes: (f) Hutchings, M. G.; Paget, W. E.; Smith, K. J. Chem. Res. (S) 1983, 31. See also: (g) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. Pentadienyltrichlorosilane: (h) Kobayashi, S.; Nishio, K. Chem. Lett. 1994, 1773. (i) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
12. Pentadienylzincs: (a) Gérard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924. (b) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101. (c) Kang, S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun. 1996, 26, 1493. (d) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667. Pentadienylmagnesiums: (e) Yasuda, H.; Yamauchi, M.; Nakamura, A.; Sei, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1089. Pentadienylberylliums: ref. 3b. Pentadienylboranes: (f) Hutchings, M. G.; Paget, W. E.; Smith, K. J. Chem. Res. (S) 1983, 31. See also: (g) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. Pentadienyltrichlorosilane: (h) Kobayashi, S.; Nishio, K. Chem. Lett. 1994, 1773. (i) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
13. Pentadienylzincs: (a) Gérard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924. (b) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101. (c) Kang, S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun. 1996, 26, 1493. (d) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667. Pentadienylmagnesiums: (e) Yasuda, H.; Yamauchi, M.; Nakamura, A.; Sei, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1089. Pentadienylberylliums: ref. 3b. Pentadienylboranes: (f) Hutchings, M. G.; Paget, W. E.; Smith, K. J. Chem. Res. (S) 1983, 31. See also: (g) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. Pentadienyltrichlorosilane: (h) Kobayashi, S.; Nishio, K. Chem. Lett. 1994, 1773. (i) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
14. Pentadienylzincs: (a) Gérard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924. (b) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101. (c) Kang, S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun. 1996, 26, 1493. (d) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667. Pentadienylmagnesiums: (e) Yasuda, H.; Yamauchi, M.; Nakamura, A.; Sei, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1089. Pentadienylberylliums: ref. 3b. Pentadienylboranes: (f) Hutchings, M. G.; Paget, W. E.; Smith, K. J. Chem. Res. (S) 1983, 31. See also: (g) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. Pentadienyltrichlorosilane: (h) Kobayashi, S.; Nishio, K. Chem. Lett. 1994, 1773. (i) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
15. Pentadienylzincs: (a) Gérard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924. (b) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101. (c) Kang, S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun. 1996, 26, 1493. (d) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667. Pentadienylmagnesiums: (e) Yasuda, H.; Yamauchi, M.; Nakamura, A.; Sei, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1089. Pentadienylberylliums: ref. 3b. Pentadienylboranes: (f) Hutchings, M. G.; Paget, W. E.; Smith, K. J. Chem. Res. (S) 1983, 31. See also: (g) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. Pentadienyltrichlorosilane: (h) Kobayashi, S.; Nishio, K. Chem. Lett. 1994, 1773. (i) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
16. Pentadienylzincs: (a) Gérard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924. (b) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101. (c) Kang, S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun. 1996, 26, 1493. (d) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667. Pentadienylmagnesiums: (e) Yasuda, H.; Yamauchi, M.; Nakamura, A.; Sei, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1089. Pentadienylberylliums: ref. 3b. Pentadienylboranes: (f) Hutchings, M. G.; Paget, W. E.; Smith, K. J. Chem. Res. (S) 1983, 31. See also: (g) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. Pentadienyltrichlorosilane: (h) Kobayashi, S.; Nishio, K. Chem. Lett. 1994, 1773. (i) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
17. Pentadienylzincs: (a) Gérard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924. (b) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101. (c) Kang, S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun. 1996, 26, 1493. (d) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667. Pentadienylmagnesiums: (e) Yasuda, H.; Yamauchi, M.; Nakamura, A.; Sei, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1089. Pentadienylberylliums: ref. 3b. Pentadienylboranes: (f) Hutchings, M. G.; Paget, W. E.; Smith, K. J. Chem. Res. (S) 1983, 31. See also: (g) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. Pentadienyltrichlorosilane: (h) Kobayashi, S.; Nishio, K. Chem. Lett. 1994, 1773. (i) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
18. Pentadienylzincs: (a) Gérard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924. (b) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101. (c) Kang, S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun. 1996, 26, 1493. (d) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667. Pentadienylmagnesiums: (e) Yasuda, H.; Yamauchi, M.; Nakamura, A.; Sei, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1089. Pentadienylberylliums: ref. 3b. Pentadienylboranes: (f) Hutchings, M. G.; Paget, W. E.; Smith, K. J. Chem. Res. (S) 1983, 31. See also: (g) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. Pentadienyltrichlorosilane: (h) Kobayashi, S.; Nishio, K. Chem. Lett. 1994, 1773. (i) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
19. Pentadienylzincs: (a) Gérard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924. (b) Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101. (c) Kang, S.-K.; Kim, D.-Y.; Hong, R.-K.; Ho, P.-S. Synth. Commun. 1996, 26, 1493. (d) Jung, M. E.; Nichols, C. J. Tetrahedron Lett. 1996, 37, 7667. Pentadienylmagnesiums: (e) Yasuda, H.; Yamauchi, M.; Nakamura, A.; Sei, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1089. Pentadienylberylliums: ref. 3b. Pentadienylboranes: (f) Hutchings, M. G.; Paget, W. E.; Smith, K. J. Chem. Res. (S) 1983, 31. See also: (g) Fujita, K.; Schlosser, M. Helv. Chim. Acta 1982, 65, 1258. Pentadienyltrichlorosilane: (h) Kobayashi, S.; Nishio, K. Chem. Lett. 1994, 1773. (i) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620.
20. 2: Nishigaichi, Y.; Fujimoto, M.; Takuwa, A. Synlett 1994, 731.
21. 2: Nishigaichi, Y.; Fujimoto, M.; Takuwa, A. Synlett 1994, 731.
22. 3SnCl in ether, for R = n-Bu, E:Z = 97:3; for R = Me, E:Z = 90:10. Preparation and spectral data of these pentadienylstannanes: (a) Seyferth, D.; Goldman, E. W.; Pornet, J. J. Organomet. Chem. 1981, 208, 189. (b) Paz-Sandoval, M. d. l. A.; Powell, P. J. Organomet. Chem. 1981, 219, 81. (c) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Chem. Lett. 1986, 1857. (d) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Org. Synth. 1993, 71, 118.
23. 3SnCl in ether, for R = n-Bu, E:Z = 97:3; for R = Me, E:Z = 90:10. Preparation and spectral data of these pentadienylstannanes: (a) Seyferth, D.; Goldman, E. W.; Pornet, J. J. Organomet. Chem. 1981, 208, 189. (b) Paz-Sandoval, M. d. l. A.; Powell, P. J. Organomet. Chem. 1981, 219, 81. (c) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Chem. Lett. 1986, 1857. (d) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Org. Synth. 1993, 71, 118.
24. 3SnCl in ether, for R = n-Bu, E:Z = 97:3; for R = Me, E:Z = 90:10. Preparation and spectral data of these pentadienylstannanes: (a) Seyferth, D.; Goldman, E. W.; Pornet, J. J. Organomet. Chem. 1981, 208, 189. (b) Paz-Sandoval, M. d. l. A.; Powell, P. J. Organomet. Chem. 1981, 219, 81. (c) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Chem. Lett. 1986, 1857. (d) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Org. Synth. 1993, 71, 118.
25. 3SnCl in ether, for R = n-Bu, E:Z = 97:3; for R = Me, E:Z = 90:10. Preparation and spectral data of these pentadienylstannanes: (a) Seyferth, D.; Goldman, E. W.; Pornet, J. J. Organomet. Chem. 1981, 208, 189. (b) Paz-Sandoval, M. d. l. A.; Powell, P. J. Organomet. Chem. 1981, 219, 81. (c) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Chem. Lett. 1986, 1857. (d) Naruta, Y.; Nishigaichi, Y.; Maruyama, K. Org. Synth. 1993, 71, 118.
26. Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723.
27. Yanagisawa, A.; Ishiba, A.; Nakashima, H.; Yamamoto, H. Synlett 1997, 88.
28. In general, reactions of allylic tin compounds with aldehydes catalyzed by bis(triphenylphosphine)-silver(I) complex give higher yields in aqueous solvent than in anhydrous solvent, see ref. 6.