Highly efficient synthesis of allylic alcohols having an α-alkoxyalkyl group at their β-position via regioselective addition reaction of titanium-propargyl ether complexes with carbonyl compounds

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7275-7278

  Yamashita, Koki ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; ALKENE DERIVATIVE; POLYENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030607154     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01647-4     Document Type: Article

References (32)

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10. (i) Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981.
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12. (k) Kataoka, Y.; Miyai, J.; Tezuka, M.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 6796-6802; see also ref 2h.
13. i PrMgX reagent, see: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216; Urabe, H.; Takeda, T.; Sato, F. Tetrahedron Lett. 1996, 37, 1253-1256; Yamazaki, T.; Kasatkin A.; Kawanaka, Y.; Sato, F. J. Org. Chem. 1996, 61, 2266-2267; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F.; Tetrahedon Lett. 1996, 37, 1849-1852 ; Gao, Y.; Harada, K.; Sato, F. J. Chem. Soc. Chem. Commun. 1996, 533-534 and references cited there in.
14. i PrMgX reagent, see: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216; Urabe, H.; Takeda, T.; Sato, F. Tetrahedron Lett. 1996, 37, 1253-1256; Yamazaki, T.; Kasatkin A.; Kawanaka, Y.; Sato, F. J. Org. Chem. 1996, 61, 2266-2267; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F.; Tetrahedon Lett. 1996, 37, 1849-1852 ; Gao, Y.; Harada, K.; Sato, F. J. Chem. Soc. Chem. Commun. 1996, 533-534 and references cited there in.
15. i PrMgX reagent, see: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216; Urabe, H.; Takeda, T.; Sato, F. Tetrahedron Lett. 1996, 37, 1253-1256; Yamazaki, T.; Kasatkin A.; Kawanaka, Y.; Sato, F. J. Org. Chem. 1996, 61, 2266-2267; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F.; Tetrahedon Lett. 1996, 37, 1849-1852 ; Gao, Y.; Harada, K.; Sato, F. J. Chem. Soc. Chem. Commun. 1996, 533-534 and references cited there in.
16. i PrMgX reagent, see: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216; Urabe, H.; Takeda, T.; Sato, F. Tetrahedron Lett. 1996, 37, 1253-1256; Yamazaki, T.; Kasatkin A.; Kawanaka, Y.; Sato, F. J. Org. Chem. 1996, 61, 2266-2267; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F.; Tetrahedon Lett. 1996, 37, 1849-1852 ; Gao, Y.; Harada, K.; Sato, F. J. Chem. Soc. Chem. Commun. 1996, 533-534 and references cited there in.
17. i PrMgX reagent, see: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216; Urabe, H.; Takeda, T.; Sato, F. Tetrahedron Lett. 1996, 37, 1253-1256; Yamazaki, T.; Kasatkin A.; Kawanaka, Y.; Sato, F. J. Org. Chem. 1996, 61, 2266-2267; Kasatkin, A.; Kobayashi, K.; Okamoto, S.; Sato, F.; Tetrahedon Lett. 1996, 37, 1849-1852 ; Gao, Y.; Harada, K.; Sato, F. J. Chem. Soc. Chem. Commun. 1996, 533-534 and references cited there in.
18. 4. The reaction of 2a with HCHO afforded complicated mixtures including the corresponding 4 in 18% yield.
19. 4 and concentrated in vacuo. The resulting oil was purified by chromatography on silica gel to give the corresponding 4 (0.113 g) in 78%.
20. 6. Synthesis of 5 from propargyl alcohols can be readily carried out using hydromagnesiation reaction. see: Sato, F.; Ishikawa, H.; Watanabe, H.; Miyake, T.; Sato. M. J. Chem. Soc. Chem. Commun. 1981, 22, 718-720; Sato, F.; Watanabe, H.; Tanaka, Y.; Sato, M. J. Chem. Soc. Chem. Commun. 1982, 1126-1127; Sato, F.; Kobayashi, Y. In Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons Inc.: New York, 1990; Vol. 69, pp. 106-112.
21. 6. Synthesis of 5 from propargyl alcohols can be readily carried out using hydromagnesiation reaction. see: Sato, F.; Ishikawa, H.; Watanabe, H.; Miyake, T.; Sato. M. J. Chem. Soc. Chem. Commun. 1981, 22, 718-720; Sato, F.; Watanabe, H.; Tanaka, Y.; Sato, M. J. Chem. Soc. Chem. Commun. 1982, 1126-1127; Sato, F.; Kobayashi, Y. In Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons Inc.: New York, 1990; Vol. 69, pp. 106-112.
22. 6. Synthesis of 5 from propargyl alcohols can be readily carried out using hydromagnesiation reaction. see: Sato, F.; Ishikawa, H.; Watanabe, H.; Miyake, T.; Sato. M. J. Chem. Soc. Chem. Commun. 1981, 22, 718-720; Sato, F.; Watanabe, H.; Tanaka, Y.; Sato, M. J. Chem. Soc. Chem. Commun. 1982, 1126-1127; Sato, F.; Kobayashi, Y. In Organic Synthesis; Paquette, L. A., Ed.; John Wiley & Sons Inc.: New York, 1990; Vol. 69, pp. 106-112.
23. 7. For efficient potential methods for synthesizing 4 from readily available starting materials, see: Corey, E. J.; Achiwa, K.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 4318-4320; Corey, E. J.; Kirst, H. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1970, 92, 6314-6319; Alexakis, A.; Normant, J. F.; Villieras, J. J. Mol. Catal. 1975, 1, 43-58; Marino, J. P.; Linderman, R. J. J. Org. Chem. 1983, 48, 4621-4628; see also ref 2k.
24. 7. For efficient potential methods for synthesizing 4 from readily available starting materials, see: Corey, E. J.; Achiwa, K.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 4318-4320; Corey, E. J.; Kirst, H. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1970, 92, 6314-6319; Alexakis, A.; Normant, J. F.; Villieras, J. J. Mol. Catal. 1975, 1, 43-58; Marino, J. P.; Linderman, R. J. J. Org. Chem. 1983, 48, 4621-4628; see also ref 2k.
25. 7. For efficient potential methods for synthesizing 4 from readily available starting materials, see: Corey, E. J.; Achiwa, K.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 4318-4320; Corey, E. J.; Kirst, H. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1970, 92, 6314-6319; Alexakis, A.; Normant, J. F.; Villieras, J. J. Mol. Catal. 1975, 1, 43-58; Marino, J. P.; Linderman, R. J. J. Org. Chem. 1983, 48, 4621-4628; see also ref 2k.
26. 7. For efficient potential methods for synthesizing 4 from readily available starting materials, see: Corey, E. J.; Achiwa, K.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 4318-4320; Corey, E. J.; Kirst, H. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1970, 92, 6314-6319; Alexakis, A.; Normant, J. F.; Villieras, J. J. Mol. Catal. 1975, 1, 43-58; Marino, J. P.; Linderman, R. J. J. Org. Chem. 1983, 48, 4621-4628; see also ref 2k.
27. 8. Frater, G.; Wenger, J. Helv. Chim. Acta 1984, 67, 1702-1706; Wada, E.; Fujiwara, I.; Kanemasa, S.; Tsuge, O. Bull. Chem. Soc. Jpn. 1987, 60, 325-334; Hatakeyama, S.; Sugawara, K.; Takano, S. Tetrahedron Lett. 1991, 32, 4513-4516; Brown, P. A.; Bonnert, R. V.; Jenkins, P. R.; Lawrence, N. J.; Selim, M. R. J. Chem. Soc. Perkin. Trans. 1. 1991, 1893-1900; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc. Chem. Commun. 1992, 953-955; Bloch, R.; C-Gradoz, N. J. Org. Chem. 1994, 59, 4162-4169.
28. 8. Frater, G.; Wenger, J. Helv. Chim. Acta 1984, 67, 1702-1706; Wada, E.; Fujiwara, I.; Kanemasa, S.; Tsuge, O. Bull. Chem. Soc. Jpn. 1987, 60, 325-334; Hatakeyama, S.; Sugawara, K.; Takano, S. Tetrahedron Lett. 1991, 32, 4513-4516; Brown, P. A.; Bonnert, R. V.; Jenkins, P. R.; Lawrence, N. J.; Selim, M. R. J. Chem. Soc. Perkin. Trans. 1. 1991, 1893-1900; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc. Chem. Commun. 1992, 953-955; Bloch, R.; C-Gradoz, N. J. Org. Chem. 1994, 59, 4162-4169.
29. 8. Frater, G.; Wenger, J. Helv. Chim. Acta 1984, 67, 1702-1706; Wada, E.; Fujiwara, I.; Kanemasa, S.; Tsuge, O. Bull. Chem. Soc. Jpn. 1987, 60, 325-334; Hatakeyama, S.; Sugawara, K.; Takano, S. Tetrahedron Lett. 1991, 32, 4513-4516; Brown, P. A.; Bonnert, R. V.; Jenkins, P. R.; Lawrence, N. J.; Selim, M. R. J. Chem. Soc. Perkin. Trans. 1. 1991, 1893-1900; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc. Chem. Commun. 1992, 953-955; Bloch, R.; C-Gradoz, N. J. Org. Chem. 1994, 59, 4162-4169.
30. 8. Frater, G.; Wenger, J. Helv. Chim. Acta 1984, 67, 1702-1706; Wada, E.; Fujiwara, I.; Kanemasa, S.; Tsuge, O. Bull. Chem. Soc. Jpn. 1987, 60, 325-334; Hatakeyama, S.; Sugawara, K.; Takano, S. Tetrahedron Lett. 1991, 32, 4513-4516; Brown, P. A.; Bonnert, R. V.; Jenkins, P. R.; Lawrence, N. J.; Selim, M. R. J. Chem. Soc. Perkin. Trans. 1. 1991, 1893-1900; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc. Chem. Commun. 1992, 953-955; Bloch, R.; C-Gradoz, N. J. Org. Chem. 1994, 59, 4162-4169.
31. 8. Frater, G.; Wenger, J. Helv. Chim. Acta 1984, 67, 1702-1706; Wada, E.; Fujiwara, I.; Kanemasa, S.; Tsuge, O. Bull. Chem. Soc. Jpn. 1987, 60, 325-334; Hatakeyama, S.; Sugawara, K.; Takano, S. Tetrahedron Lett. 1991, 32, 4513-4516; Brown, P. A.; Bonnert, R. V.; Jenkins, P. R.; Lawrence, N. J.; Selim, M. R. J. Chem. Soc. Perkin. Trans. 1. 1991, 1893-1900; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc. Chem. Commun. 1992, 953-955; Bloch, R.; C-Gradoz, N. J. Org. Chem. 1994, 59, 4162-4169.
32. 8. Frater, G.; Wenger, J. Helv. Chim. Acta 1984, 67, 1702-1706; Wada, E.; Fujiwara, I.; Kanemasa, S.; Tsuge, O. Bull. Chem. Soc. Jpn. 1987, 60, 325-334; Hatakeyama, S.; Sugawara, K.; Takano, S. Tetrahedron Lett. 1991, 32, 4513-4516; Brown, P. A.; Bonnert, R. V.; Jenkins, P. R.; Lawrence, N. J.; Selim, M. R. J. Chem. Soc. Perkin. Trans. 1. 1991, 1893-1900; Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc. Chem. Commun. 1992, 953-955; Bloch, R.; C-Gradoz, N. J. Org. Chem. 1994, 59, 4162-4169.