Zinc-Mediated Allylation of N-Protected α-Amino Aldehydes in Aqueous Solution. Stereoselective Synthesis of Anti- and Syn-β-Amino Alcohols with Functionalized Allyl Groups

Synlett

Volumn 1997, Issue 4, 1997, Pages 353-354

  Hanessian, Stephen ^a   Park, Haeil ^a   Yang, Rui Yang ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002851824     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-804     Document Type: Article

References (31)

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5. See for example, Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104; Durant, A.; Deplancke, J.-L.; Winard, R.; Reisse, J. Tetrahedron Lett., 1995, 36, 4257; Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett., 1992, 33, 97; Ahonen, M.; Sjöholm, R. Chemistry Lett. 1995, 341; Sjöholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc. Chem. Commun. 1994, 1217; F. Waldmann, H. Synlett, 1990, 627; Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649; Kunz, T.; Reißig, H.-U. Liebigs Ann. Chem. 1989, 891;
6. See for example, Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104; Durant, A.; Deplancke, J.-L.; Winard, R.; Reisse, J. Tetrahedron Lett., 1995, 36, 4257; Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett., 1992, 33, 97; Ahonen, M.; Sjöholm, R. Chemistry Lett. 1995, 341; Sjöholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc. Chem. Commun. 1994, 1217; F. Waldmann, H. Synlett, 1990, 627; Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649; Kunz, T.; Reißig, H.-U. Liebigs Ann. Chem. 1989, 891;
7. See for example, Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104; Durant, A.; Deplancke, J.-L.; Winard, R.; Reisse, J. Tetrahedron Lett., 1995, 36, 4257; Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett., 1992, 33, 97; Ahonen, M.; Sjöholm, R. Chemistry Lett. 1995, 341; Sjöholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc. Chem. Commun. 1994, 1217; F. Waldmann, H. Synlett, 1990, 627; Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649; Kunz, T.; Reißig, H.-U. Liebigs Ann. Chem. 1989, 891;
8. See for example, Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104; Durant, A.; Deplancke, J.-L.; Winard, R.; Reisse, J. Tetrahedron Lett., 1995, 36, 4257; Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett., 1992, 33, 97; Ahonen, M.; Sjöholm, R. Chemistry Lett. 1995, 341; Sjöholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc. Chem. Commun. 1994, 1217; F. Waldmann, H. Synlett, 1990, 627; Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649; Kunz, T.; Reißig, H.-U. Liebigs Ann. Chem. 1989, 891;
9. See for example, Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104; Durant, A.; Deplancke, J.-L.; Winard, R.; Reisse, J. Tetrahedron Lett., 1995, 36, 4257; Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett., 1992, 33, 97; Ahonen, M.; Sjöholm, R. Chemistry Lett. 1995, 341; Sjöholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc. Chem. Commun. 1994, 1217; F. Waldmann, H. Synlett, 1990, 627; Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649; Kunz, T.; Reißig, H.-U. Liebigs Ann. Chem. 1989, 891;
10. See for example, Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104; Durant, A.; Deplancke, J.-L.; Winard, R.; Reisse, J. Tetrahedron Lett., 1995, 36, 4257; Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett., 1992, 33, 97; Ahonen, M.; Sjöholm, R. Chemistry Lett. 1995, 341; Sjöholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc. Chem. Commun. 1994, 1217; F. Waldmann, H. Synlett, 1990, 627; Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649; Kunz, T.; Reißig, H.-U. Liebigs Ann. Chem. 1989, 891;
11. See for example, Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104; Durant, A.; Deplancke, J.-L.; Winard, R.; Reisse, J. Tetrahedron Lett., 1995, 36, 4257; Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett., 1992, 33, 97; Ahonen, M.; Sjöholm, R. Chemistry Lett. 1995, 341; Sjöholm, R.; Rairama, R.; Ahonen, M. J. Chem. Soc. Chem. Commun. 1994, 1217; F. Waldmann, H. Synlett, 1990, 627; Chan, T. H.; Li, C. J. Organometallics 1990, 9, 2649; Kunz, T.; Reißig, H.-U. Liebigs Ann. Chem. 1989, 891;
12. (i) Petrier, C.; Einhorn, J.; Luche, J. L. Tetrahedron Lett. 1985, 26, 910; Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697.
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19. Ciapetti, P.; Falorni, M.; Taddei, M. Tetrahedron 1996, 52, 7379.
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21. For a discussion of mechanistic issues, see, Paquette, L.A.; Mitzel, T.M. J. Am. Chem. Soc. 1996, 118, 1931.
22. O'Brien, P.; Warren, S. Tetrahedron Lett. 1996, 37, 4271; see also ref. 3a.
23. The allylation of α-amino aldehydes bearing an N-Boc protecting group gave products with poor diastereoselectivities, a) allyl bromide, 90%; 26% de. b) 2-bromomethyl-1-propene, 90%; 44% de. c) (2-bromomethyl)acrylic acid, 92%; 20% de. d) methyl (2-bromomethyl)acrylic acid, 94%; 20% de. e) tert-butyl (2-bromomethyl)acrylic acid, 85%; 20% de. f) 4-bromo-2-methyl-2-butene, 95%; 41% de.
24. Enantiomerically pure or highly enriched anti- and syn-β-amino alcohols were obtained by silica gel flash column chromatography (hexane:ethyl acetate=20:1) after aqueous workup.
25. Reetz, M.T.; Drews, M.W.; Lennick, K.; Schmitz, A. Tetrahedron: Asymmetry, 1996, 1, 375; Alexander, C. W.; Liotta, D. C. Tetrahedron Lett. 1996, 37, 1961. Captain, L. F.; Xia, X.; Liotta, D. C. Tetrahedron Lett. 1996, 37, 4293.
26. Reetz, M.T.; Drews, M.W.; Lennick, K.; Schmitz, A. Tetrahedron: Asymmetry, 1996, 1, 375; Alexander, C. W.; Liotta, D. C. Tetrahedron Lett. 1996, 37, 1961. Captain, L. F.; Xia, X.; Liotta, D. C. Tetrahedron Lett. 1996, 37, 4293.
27. Reetz, M.T.; Drews, M.W.; Lennick, K.; Schmitz, A. Tetrahedron: Asymmetry, 1996, 1, 375; Alexander, C. W.; Liotta, D. C. Tetrahedron Lett. 1996, 37, 1961. Captain, L. F.; Xia, X.; Liotta, D. C. Tetrahedron Lett. 1996, 37, 4293.
28. Bloch, R.; Brillet, C. Synlett, 1991, 829; Griffith, W.P.; Ley, S.V.; Whitcombe, G.P.; White, A.D.; J. Chem. Soc., Chem. Comm., 1987, 1625; Lagu, B. R.; Lotta, D. C. Tetrahedron Lett. 1994, 35, 547; Diederich, A. M.; Ryckman, D. M. Tetrahedron Lett. 1993, 34, 6169.
29. Bloch, R.; Brillet, C. Synlett, 1991, 829; Griffith, W.P.; Ley, S.V.; Whitcombe, G.P.; White, A.D.; J. Chem. Soc., Chem. Comm., 1987, 1625; Lagu, B. R.; Lotta, D. C. Tetrahedron Lett. 1994, 35, 547; Diederich, A. M.; Ryckman, D. M. Tetrahedron Lett. 1993, 34, 6169.
30. Bloch, R.; Brillet, C. Synlett, 1991, 829; Griffith, W.P.; Ley, S.V.; Whitcombe, G.P.; White, A.D.; J. Chem. Soc., Chem. Comm., 1987, 1625; Lagu, B. R.; Lotta, D. C. Tetrahedron Lett. 1994, 35, 547; Diederich, A. M.; Ryckman, D. M. Tetrahedron Lett. 1993, 34, 6169.
31. Bloch, R.; Brillet, C. Synlett, 1991, 829; Griffith, W.P.; Ley, S.V.; Whitcombe, G.P.; White, A.D.; J. Chem. Soc., Chem. Comm., 1987, 1625; Lagu, B. R.; Lotta, D. C. Tetrahedron Lett. 1994, 35, 547; Diederich, A. M.; Ryckman, D. M. Tetrahedron Lett. 1993, 34, 6169.