Comparative study of the diastereoselective addition of allenyl zinc reagents to α-alkoxy (or silyloxy) aldehydes and imines. A straightforward synthesis of amino alcohols from imines

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6553-6560

  Poisson, Jean François ^a   Normant, Jean F ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALLENE DERIVATIVE; AMINOALCOHOL; IMINE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034613348     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo005509r     Document Type: Article

References (48)

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31. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
32. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207-2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
33. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
34. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
35. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
36. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835-1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
37. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
38. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
39. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
40. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
41. For generality, see: (a) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon Press, New York, 1991; Vol. 2, p 984. (b) Bloch, R. Chem. Rev. 1998, 1407-1438. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 2207- 2293. With allyltitanium, see: (d) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. For allylzinc, see: (e) Baside, T.; Bocum, A.; Savoia, D.; Umani-ronchi, A. J. Org. Chem. 1994, 59, 7766-7773. (f) Dembele, Y. A.; Beland, C.; Hitchcock, P.; Villieras, J. Tetrahedron: Asymmetry 1992, 8, 351-354. (g) Nyzam, V.; Beland, C.; Zammatio, F.; Villieras, J. Tetrahedron: Asymmetry 1996, 8, 1835- 1843. (h) Chtara, R. A.; Moreau, J. L.; Gaudemar, M. C. R. Acad. Sci. Ser. C 1975, 280, 1157-1159. (i) Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778-7786. (j) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814-816. For allyl Boron see: (k) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Am. Chem. Soc. 1984, 106, 5031-5033. (l) Yamamoto, Y.; Komatsu, T.; Muruyama, K. J. Org. Chem. 1985, 50, 3115-3121.
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