Application of the Blaise reaction: Stereoselective synthesis of (4R)- tert-butyl 3-amino-4-trimethylsilyloxy-2-alkenoates from (R)-cyanohydrins

Tetrahedron Asymmetry

Volumn 9, Issue 5, 1998, Pages 805-815

  Syed, Jana ^a   Förster, Siegfried ^a   Effenberger, Franz ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMMONIUM CHLORIDE; BETA AMINO GAMMA HYDROXYBUTYROLACTONE; CYANOHYDRIN; DICHLOROMETHANE; ESTER; HYDROCHLORIC ACID; LACTONE; NITRILE; REAGENT; TERT BUTYL 2 BROMOESTER; TERT BUTYL 3 AMINO 4 TRIMETHYLSILOXY 2 ALKENOATE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; HYDROGENATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032513158     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00039-1     Document Type: Article

References (46)

1. 1. Enzyme-catalyzed Reactions, Part 32. Part 31: Effenberger, F.; Graef, B. W. J. Biotechnol., in press.
2. 2. (a) Effenberger, F.; Gutterer, B.; Ziegler, T. Liebigs Ann. Chem. 1991, 269-273.
3. (b) Effenberger, F. Angew. Chem. 1994, 106, 1609-1619. Angew. Chem. Int. Ed. Engl. 1994, 33, 1555-1564.
4. (b) Effenberger, F. Angew. Chem. 1994, 106, 1609-1619. Angew. Chem. Int. Ed. Engl. 1994, 33, 1555-1564.
5. (c) Brussee, J.; Dofferhoff, F.; Kruse, C. G.; van der Gen, A. Tetrahedron 1990, 46, 1653-1658.
6. (d) Jackson, W. R.; Jacobs, H. A.; Matthews, B. R.; Jayatilake, G. S.; Watson, K. G. Tetrahedron Lett. 1990, 31, 1447-1450.
7. 3. Effenberger, F.; Gutterer, B.; Syed, J. Tetrahedron: Asymmetry 1995, 6, 2933-2943.
8. 4. (a) Blaise, E. E. C. R. Hebd. Seances Acad. Sci. 1901, 132, 478 and 978.
9. (b) Cason, J.; Rinehart Jr., K. L.; Thornton Jr., S. D. J. Org. Chem. 1953, 18, 1594-1600.
10. (c) Kagan, H. B.; Suen, Y.-H. Bull. Soc. Chim. Fr. 1966, 1819-1822.
11. (d) Hannick, S. M.; Kishi, Y. J. Org. Chem. 1983, 48, 3833-3835.
12. 5. (a) Anderson, J. R.; Edwards, R. L. J. Chem. Soc., Perkin Trans 1 1982, 215-221.
13. (b) Krepski, L. R.; Lynch, L. E.; Heilmann, S. M.; Rasmussen, J. K. Tetrahedron Lett. 1985, 26, 981-984.
14. 6. (a) Kitazume, T. J. Fluorine Chem. 1987, 35, 287-294.
15. (b) Duffield, J. J.; Regan, A. C. Tetrahedron: Asymmetry 1996, 7, 663-666.
16. 7. Lee, A. S.-Y.; Cheng, R.-Y. Tetrahedron Lett. 1997, 38, 443-446.
17. 8. (a) Bewley, C. A.; Faulkner, D. J. J. Org. Chem. 1994, 59, 4849-4852.
18. (b) Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Wälchli, M. J. Am. Chem. Soc. 1989, 111, 2582-2588.
19. (c) Wakamiya, T.; Shiba, T.; Kaneko, T. Bull. Chem. Soc. Jpn 1972, 45, 3668-3672.
20. 9. (a) Shimojima, Y.; Hayashi, H.; Ooka, T.; Shibukawa, M. Tetrahedron 1984, 40, 2519-2527.
21. (b) Shinozaki, K.; Mizuno, K.; Masaki, Y. Heterocycles 1996, 43, 11-14.
22. 10. Seki, M.; Moriya, T.; Matsumoto, K. Agric. Biol. Chem. 1987, 51, 3033-3038.
23. 11. (a) Takahashi, Y.; Hasegawa, S.; Izawa, T.; Kobayashi, S.; Ohno, M. Chem. Pharm. Bull. 1986, 34, 3020-3024.
24. (b) Nitta, H.; Hatanaka, M.; Ishimaru, T. J. Chem. Soc., Chem. Commun. 1987, 51-52.
25. 12. McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952.
26. 13. Hoff, H.; Drautz, H.; Fiedler, H.-P; Zähner, H.; Schultz, J. E.; Keller-Schierlein, W.; Philipps, S.; Ritzau, M.; Zeeck, A. J. Antibiotics 1992, 45, 1096-1107.
27. 14. Lawson, A. (National Research Development Corp.) Brit. 772,836, Apr. 17, 1957; Chem. Abstr. 1958, 52, 1242b.
28. 14. Lawson, A. (National Research Development Corp.) Brit. 772,836, Apr. 17, 1957; Chem. Abstr. 1958, 52, 1242b.
29. 15. Rathke, M. W.; Lindert, A. J. Org. Chem. 1970, 35, 3966-3967.
30. 16. Vaughan, W. R.; Bernstein, S. C.; Lorber, M. E. J. Org. Chem. 1965, 30, 1790-1795.
31. 17. LeGoff, E. J. Org. Chem. 1964, 29, 2048-2050.
32. 18. Cornforth, D. A.; Opara, A. E.; Read, G. J. Chem. Soc. C 1969, 2799-2805.
33. 19. (a) Sheldrick, G. SHELXS-86, Institute of Inorganic Chemistry, University of Göttingen, 1986.
34. (b) Stewart, J. M.; Dickinson, P. A.; Ammon, H. L.; Flack, H.; Heck, H. XRAY-76, Tech. Kept. TR-446, University of Maryland, Computer Center, College Park MD, 1976.
35. (c) Johnson, C. K. A Fortran Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Tech. Rept. ORNL-5138, Oak Ridge National Laboratory, Oak Ridge TN, 1971.
36. 20. (a) Liska, K. J. J. Pharm. Sci. 1964, 53, 1427-1428.
37. (b) Augustine, R. L.; Belling, R. F.; Gustavsen, A. J. J. Org. Chem. 1968, 33, 1287-1288.
38. 21. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897-2904.
39. 22. Gribble, G. W.; Nutaitis, C. F. Org. Prep. Proced. Int. 1985, 17, 317-384.
40. 23. (a) Brussee, J. Thesis, Universität Leiden, 1992.
41. (b) Clemo, N. G.; Pattenden, G. J. Chem. Soc., Perkin Trans 1 1985, 2407-2411.
42. (c) Ladenburg, K.; Folkers, K.; Major, R. T. J. Am. Chem. Soc. 1936, 58, 1292-1294.
43. 24. Pavlov, S.; Bogavac, M.; Arsenijevic, V. Bull. Soc. Chim. Fr. 1974, 2985-2986.
44. 25. Rasmussen, J. K.; Heilmann, S. M. Synthesis 1978, 219-221.
45. 26. (a) Eichhorn, J. Dissertation, Universität Stuttgart, 1995.
46. (b) Effenberger, F.; Jäger, J. J. Org. Chem. 1997, 62, 3867-3873.