A stereoselective synthesis of (E)-allylic alcohols via the hydromagnesiation of alkynylsilanes

Journal of Chemical Research - Part S

Volumn , Issue 5, 2003, Pages 296-298

  Cai, Mingzhong ^a   Peng, Chunyun ^a   Zhao, Hong ^b   Hao, Wenyan ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

^b SHANGRAO NORMAL UNIVERSITY   (China)

Author keywords

(E) allylic alcohol; Alkynylsilane; Desilylation reaction; Hydromagnesiation; Stereoselective synthesis

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALKYNYL GROUP; ALLYL COMPOUND; GRIGNARD REAGENT; KETONE; POTASSIUM FLUORIDE; REAGENT; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DESILYLATION; HYDROMAGNESIATION; ISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141679144     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823403103173877     Document Type: Article

References (28)

1. T.K. Jones and S.E. Denmark, Org. Synth., 1990, Coll. Vol. 7, 524; D.J. Faulkner, Synthesis, 1971, 175; J. Reucroft and P.G. Sammes, Q. Rev. Chem. Soc., 1971, 25, 135; R.M. Magid, O.S. Fruchey, W.L. Johnson and T.G. Allen, J. Org. Chem., 1979, 44, 359; E.J. Corey, C.V. Kim and M. Takeda, Tetrahedron Lett., 1972, 4339; S. Okamoto, H. Tsujiyama, T. Yoshino and F. Sato, Tetrahedron Lett., 1991, 32, 5789.
2. T.K. Jones and S.E. Denmark, Org. Synth., 1990, Coll. Vol. 7, 524; D.J. Faulkner, Synthesis, 1971, 175; J. Reucroft and P.G. Sammes, Q. Rev. Chem. Soc., 1971, 25, 135; R.M. Magid, O.S. Fruchey, W.L. Johnson and T.G. Allen, J. Org. Chem., 1979, 44, 359; E.J. Corey, C.V. Kim and M. Takeda, Tetrahedron Lett., 1972, 4339; S. Okamoto, H. Tsujiyama, T. Yoshino and F. Sato, Tetrahedron Lett., 1991, 32, 5789.
3. T.K. Jones and S.E. Denmark, Org. Synth., 1990, Coll. Vol. 7, 524; D.J. Faulkner, Synthesis, 1971, 175; J. Reucroft and P.G. Sammes, Q. Rev. Chem. Soc., 1971, 25, 135; R.M. Magid, O.S. Fruchey, W.L. Johnson and T.G. Allen, J. Org. Chem., 1979, 44, 359; E.J. Corey, C.V. Kim and M. Takeda, Tetrahedron Lett., 1972, 4339; S. Okamoto, H. Tsujiyama, T. Yoshino and F. Sato, Tetrahedron Lett., 1991, 32, 5789.
4. T.K. Jones and S.E. Denmark, Org. Synth., 1990, Coll. Vol. 7, 524; D.J. Faulkner, Synthesis, 1971, 175; J. Reucroft and P.G. Sammes, Q. Rev. Chem. Soc., 1971, 25, 135; R.M. Magid, O.S. Fruchey, W.L. Johnson and T.G. Allen, J. Org. Chem., 1979, 44, 359; E.J. Corey, C.V. Kim and M. Takeda, Tetrahedron Lett., 1972, 4339; S. Okamoto, H. Tsujiyama, T. Yoshino and F. Sato, Tetrahedron Lett., 1991, 32, 5789.
5. T.K. Jones and S.E. Denmark, Org. Synth., 1990, Coll. Vol. 7, 524; D.J. Faulkner, Synthesis, 1971, 175; J. Reucroft and P.G. Sammes, Q. Rev. Chem. Soc., 1971, 25, 135; R.M. Magid, O.S. Fruchey, W.L. Johnson and T.G. Allen, J. Org. Chem., 1979, 44, 359; E.J. Corey, C.V. Kim and M. Takeda, Tetrahedron Lett., 1972, 4339; S. Okamoto, H. Tsujiyama, T. Yoshino and F. Sato, Tetrahedron Lett., 1991, 32, 5789.
6. T.K. Jones and S.E. Denmark, Org. Synth., 1990, Coll. Vol. 7, 524; D.J. Faulkner, Synthesis, 1971, 175; J. Reucroft and P.G. Sammes, Q. Rev. Chem. Soc., 1971, 25, 135; R.M. Magid, O.S. Fruchey, W.L. Johnson and T.G. Allen, J. Org. Chem., 1979, 44, 359; E.J. Corey, C.V. Kim and M. Takeda, Tetrahedron Lett., 1972, 4339; S. Okamoto, H. Tsujiyama, T. Yoshino and F. Sato, Tetrahedron Lett., 1991, 32, 5789.
7. B. Jousseaume and J.G. Duboudin, J. Organomet. Chem., 1975, 91, C1; M. Zaidlewicz, A. Uzarewicz and R. Sarnowski, Synthesis, 1979, 62; A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu and N. Sonoda, J. Org. Chem., 1994, 59, 1600; P.A. Netland, Org. Prep. Proc. Int., 1980, 12, 216; K. Takai, Y. Kataoka and K. Utimoto, J. Org. Chem., 1990, 55, 1707; A. Kamimura and N. Ono, J. Chem. Soc., Chem. Commun., 1988, 1278; M. Yukio, S. Kazuhiko and K. Kenji, Chem. Pharm. Bull., 1985, 33, 2531; M. Julia and J.N. Verpeaux, Tetrahedron, 1983, 39, 3289.
8. B. Jousseaume and J.G. Duboudin, J. Organomet. Chem., 1975, 91, C1; M. Zaidlewicz, A. Uzarewicz and R. Sarnowski, Synthesis, 1979, 62; A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu and N. Sonoda, J. Org. Chem., 1994, 59, 1600; P.A. Netland, Org. Prep. Proc. Int., 1980, 12, 216; K. Takai, Y. Kataoka and K. Utimoto, J. Org. Chem., 1990, 55, 1707; A. Kamimura and N. Ono, J. Chem. Soc., Chem. Commun., 1988, 1278; M. Yukio, S. Kazuhiko and K. Kenji, Chem. Pharm. Bull., 1985, 33, 2531; M. Julia and J.N. Verpeaux, Tetrahedron, 1983, 39, 3289.
9. B. Jousseaume and J.G. Duboudin, J. Organomet. Chem., 1975, 91, C1; M. Zaidlewicz, A. Uzarewicz and R. Sarnowski, Synthesis, 1979, 62; A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu and N. Sonoda, J. Org. Chem., 1994, 59, 1600; P.A. Netland, Org. Prep. Proc. Int., 1980, 12, 216; K. Takai, Y. Kataoka and K. Utimoto, J. Org. Chem., 1990, 55, 1707; A. Kamimura and N. Ono, J. Chem. Soc., Chem. Commun., 1988, 1278; M. Yukio, S. Kazuhiko and K. Kenji, Chem. Pharm. Bull., 1985, 33, 2531; M. Julia and J.N. Verpeaux, Tetrahedron, 1983, 39, 3289.
10. B. Jousseaume and J.G. Duboudin, J. Organomet. Chem., 1975, 91, C1; M. Zaidlewicz, A. Uzarewicz and R. Sarnowski, Synthesis, 1979, 62; A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu and N. Sonoda, J. Org. Chem., 1994, 59, 1600; P.A. Netland, Org. Prep. Proc. Int., 1980, 12, 216; K. Takai, Y. Kataoka and K. Utimoto, J. Org. Chem., 1990, 55, 1707; A. Kamimura and N. Ono, J. Chem. Soc., Chem. Commun., 1988, 1278; M. Yukio, S. Kazuhiko and K. Kenji, Chem. Pharm. Bull., 1985, 33, 2531; M. Julia and J.N. Verpeaux, Tetrahedron, 1983, 39, 3289.
11. B. Jousseaume and J.G. Duboudin, J. Organomet. Chem., 1975, 91, C1; M. Zaidlewicz, A. Uzarewicz and R. Sarnowski, Synthesis, 1979, 62; A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu and N. Sonoda, J. Org. Chem., 1994, 59, 1600; P.A. Netland, Org. Prep. Proc. Int., 1980, 12, 216; K. Takai, Y. Kataoka and K. Utimoto, J. Org. Chem., 1990, 55, 1707; A. Kamimura and N. Ono, J. Chem. Soc., Chem. Commun., 1988, 1278; M. Yukio, S. Kazuhiko and K. Kenji, Chem. Pharm. Bull., 1985, 33, 2531; M. Julia and J.N. Verpeaux, Tetrahedron, 1983, 39, 3289.
12. B. Jousseaume and J.G. Duboudin, J. Organomet. Chem., 1975, 91, C1; M. Zaidlewicz, A. Uzarewicz and R. Sarnowski, Synthesis, 1979, 62; A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu and N. Sonoda, J. Org. Chem., 1994, 59, 1600; P.A. Netland, Org. Prep. Proc. Int., 1980, 12, 216; K. Takai, Y. Kataoka and K. Utimoto, J. Org. Chem., 1990, 55, 1707; A. Kamimura and N. Ono, J. Chem. Soc., Chem. Commun., 1988, 1278; M. Yukio, S. Kazuhiko and K. Kenji, Chem. Pharm. Bull., 1985, 33, 2531; M. Julia and J.N. Verpeaux, Tetrahedron, 1983, 39, 3289.
13. B. Jousseaume and J.G. Duboudin, J. Organomet. Chem., 1975, 91, C1; M. Zaidlewicz, A. Uzarewicz and R. Sarnowski, Synthesis, 1979, 62; A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu and N. Sonoda, J. Org. Chem., 1994, 59, 1600; P.A. Netland, Org. Prep. Proc. Int., 1980, 12, 216; K. Takai, Y. Kataoka and K. Utimoto, J. Org. Chem., 1990, 55, 1707; A. Kamimura and N. Ono, J. Chem. Soc., Chem. Commun., 1988, 1278; M. Yukio, S. Kazuhiko and K. Kenji, Chem. Pharm. Bull., 1985, 33, 2531; M. Julia and J.N. Verpeaux, Tetrahedron, 1983, 39, 3289.
14. B. Jousseaume and J.G. Duboudin, J. Organomet. Chem., 1975, 91, C1; M. Zaidlewicz, A. Uzarewicz and R. Sarnowski, Synthesis, 1979, 62; A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu and N. Sonoda, J. Org. Chem., 1994, 59, 1600; P.A. Netland, Org. Prep. Proc. Int., 1980, 12, 216; K. Takai, Y. Kataoka and K. Utimoto, J. Org. Chem., 1990, 55, 1707; A. Kamimura and N. Ono, J. Chem. Soc., Chem. Commun., 1988, 1278; M. Yukio, S. Kazuhiko and K. Kenji, Chem. Pharm. Bull., 1985, 33, 2531; M. Julia and J.N. Verpeaux, Tetrahedron, 1983, 39, 3289.
15. M.J. Kang, J.-S. Jang and S.-G. Lee, Tetrahedron Lett., 1995, 36, 8829.
16. H.C. Brown, A.S. Phadke and N.G. Bhat, Tetrahedron Lett., 1993, 34, 7845.
17. C.F. Nutaitis and J.E. Bernardo, J. Org. Chem., 1989, 54, 5629.
18. F. Sato, H. Watanabe, Y. Tanaka, T. Yamaji and M. Sato, Tetrahedron Lett., 1983, 24, 1041.
19. F. Sato, J. Organomet. Chem., 1985, 285, 53; F. Sato and H. Urabe, In: Grignard Reagents - New Developments: Hydromagnesiation of Alkenes and Alkynes; H. G. Richey, Jr., Ed.; Wiley: Chichester, 2000; p65; Y. Gao and F. Sato, J. Chem. Soc., Chem. Commun., 1995, 659.
20. F. Sato, J. Organomet. Chem., 1985, 285, 53; F. Sato and H. Urabe, In: Grignard Reagents - New Developments: Hydromagnesiation of Alkenes and Alkynes; H. G. Richey, Jr., Ed.; Wiley: Chichester, 2000; p65; Y. Gao and F. Sato, J. Chem. Soc., Chem. Commun., 1995, 659.
21. F. Sato, J. Organomet. Chem., 1985, 285, 53; F. Sato and H. Urabe, In: Grignard Reagents - New Developments: Hydromagnesiation of Alkenes and Alkynes; H. G. Richey, Jr., Ed.; Wiley: Chichester, 2000; p65; Y. Gao and F. Sato, J. Chem. Soc., Chem. Commun., 1995, 659.
22. C. Eaborn and D.R.M. Walton, J. Organomet. Chem., 1964, 2, 95.
23. T.H. Chan and I. Fleming, Synthesis, 1979, 761.
24. T.H. Chan and W. Mychajlowskij, Tetrahedron Lett., 1974, 3479; W.E. Fristad, T.R. Bailey and L.A. Paquette, J. Org. Chem., 1980, 45, 3028; R.B. Miller and M.I. Al-Hassan, J. Org. Chem., 1983, 48, 4113.
25. T.H. Chan and W. Mychajlowskij, Tetrahedron Lett., 1974, 3479; W.E. Fristad, T.R. Bailey and L.A. Paquette, J. Org. Chem., 1980, 45, 3028; R.B. Miller and M.I. Al-Hassan, J. Org. Chem., 1983, 48, 4113.
26. T.H. Chan and W. Mychajlowskij, Tetrahedron Lett., 1974, 3479; W.E. Fristad, T.R. Bailey and L.A. Paquette, J. Org. Chem., 1980, 45, 3028; R.B. Miller and M.I. Al-Hassan, J. Org. Chem., 1983, 48, 4113.
27. R.S. Rasmussen and R.R. Brattain, J. Chem. Phys., 1947, 15, 131; O.D. Shreve, M.R. Heether, H.B. Knighf and D. Swern, Analyt. Chem., 1950, 22, 1261.
28. R.S. Rasmussen and R.R. Brattain, J. Chem. Phys., 1947, 15, 131; O.D. Shreve, M.R. Heether, H.B. Knighf and D. Swern, Analyt. Chem., 1950, 22, 1261.