Zinc-Mediated Allylation of N-Protected α-Amino Aldehydes in Aqueous Solution. Stereoselective Synthesis of Phe-Phe Hydroxyethylene Dipeptide Isosteres

Synlett

Volumn 1997, Issue 4, 1997, Pages 351-352

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

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002903474     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-803     Document Type: Article

References (36)

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2. Giannis, A.; Koller, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Ocain, T. D.; Abou-Gharbia, M. Drugs of the Future, 1991, 16, 37; Greenlee, W. J. Med. Chem. Rev. 1990, 10, 173; Greenlee, W. J. Pharmaceutical Res. 1987, 4, 364; Plattner, J. J.; Kleinert, H. D. Ann. Rep. Med. Chem. 1987, 22, 63.
3. Giannis, A.; Koller, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Ocain, T. D.; Abou-Gharbia, M. Drugs of the Future, 1991, 16, 37; Greenlee, W. J. Med. Chem. Rev. 1990, 10, 173; Greenlee, W. J. Pharmaceutical Res. 1987, 4, 364; Plattner, J. J.; Kleinert, H. D. Ann. Rep. Med. Chem. 1987, 22, 63.
4. Giannis, A.; Koller, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Ocain, T. D.; Abou-Gharbia, M. Drugs of the Future, 1991, 16, 37; Greenlee, W. J. Med. Chem. Rev. 1990, 10, 173; Greenlee, W. J. Pharmaceutical Res. 1987, 4, 364; Plattner, J. J.; Kleinert, H. D. Ann. Rep. Med. Chem. 1987, 22, 63.
5. Giannis, A.; Koller, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244; Ocain, T. D.; Abou-Gharbia, M. Drugs of the Future, 1991, 16, 37; Greenlee, W. J. Med. Chem. Rev. 1990, 10, 173; Greenlee, W. J. Pharmaceutical Res. 1987, 4, 364; Plattner, J. J.; Kleinert, H. D. Ann. Rep. Med. Chem. 1987, 22, 63.
6. Thaisrivongs, S. J. Ann. Rep. Med. Chem. 1994, 29, 133; Norbeck, D. W.; Kempf, D. J. Ann. Rep. Med. Chem. 1991, 26, 141.
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25. For a typical procedure: To a stirring solution of the aldehyde (1 mmol) and the allylic bromo acid (3 mmol) in THF (2 mL) was added saturated aqueous ammonium chloride solution (10 mL). The reaction mixture was cooled to 0°C and zinc dust (6 mmol) was slowly added to the reaction mixture and stirring was continued at 0°C for 1 h. The reaction mixture was diluted with ethyl acetate (100 mL), and processed as usual. Purification of the crude product by silica gel flash column chromatography (15% ethyl acetate/hexanes) gave 5 in 90 % yield.
26. Ciapetti, P.; Falorni, M.; Taddei, M. Tetrahedron 1996, 52, 7379.
27. For a typical procedure: To a stirring suspension of CuCN (2 mmol) in THF (4 mL) was slowly added phenyllithium (4 mmol) at -78°C and the mixture was stirred at -25°C for 1 h. The reaction mixture was cooled again to -78°C and the lactone 6 (1 mmol) was added followed by chlorotrimethylsilane (4 mmol). The reaction mixture was stirred at -78°C for 2 h and the temperature was allowed to warm up to room temperature. After 16 h, the reaction mixture was quenched by adding 5% ammonia water and saturated aqueous ammonium chloride solution (1:1, 1 mL). The mixture was diluted with ethyl acetate (100 mL) and processed as usual. Purification of the residue by silica gel flash column chromatography (5% ethyl acetate/hexane) gave a mixture of syn/anti products as a colorless oil (93:7) in 80 % yield.
28. Reetz, M.T.; Drews, M.W.; Lennick, K.; Schmitz, A. Tetrahedron: Asymmetry 1990, 1, 375.
29. Bajwa, J. S. Tetrahedron Lett. 1992, 33, 2955.
30. For a typical procedure: To a stirring solution of triphenylphosphine (2 mmol) in benzene (3 mL) was added DEAD (2 mmol) at 0°C, and the reaction mixture was stirred for 1 h at room temperature. The acid 8 (1 mmol) in benzene (2 mL) was added to the above mixture and reaction was continued for 1 h at 0°C and for 14 h at room temperature. Removal of solvent in vacuo and purification of the residue by silica gel flash column chromatography (5% ethyl acetate/hexane) gave the anti product 2 as a white solid in 65% yield and the syn product 3 as a colorless oil in 24% yield.
31. The authentic sample provided by Ciba-Geigy, Basel as the acid form, was transformed to the corresponding lactone under the standard conditions.
32. See for example Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947; Melillo, D. G.; Liu, T.; Ryan, K.; Stetzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913; Mitsunobu, O. Synthesis 1981, 1.
33. See for example Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947; Melillo, D. G.; Liu, T.; Ryan, K.; Stetzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913; Mitsunobu, O. Synthesis 1981, 1.
34. See for example Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947; Melillo, D. G.; Liu, T.; Ryan, K.; Stetzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913; Mitsunobu, O. Synthesis 1981, 1.
35. For the earliest examples, see, Petrier, C.; Einhorn, J.; Luche, J. L. Tetrahedron Lett. 1985, 26, 5697. For a recent review, see Li, C.-J. Tetrahedron 1996, 52, 5643.
36. For the earliest examples, see, Petrier, C.; Einhorn, J.; Luche, J. L. Tetrahedron Lett. 1985, 26, 5697. For a recent review, see Li, C.-J. Tetrahedron 1996, 52, 5643.