Diastereoselective addition of HCN to Garner's aldehyde

Tetrahedron Asymmetry

Volumn 10, Issue 8, 1999, Pages 1617-1622

  Marcus, Jan ^a   Vandermeulen, Guido W M ^a   Brussee, Johannes ^a   Van der Gen, Arne ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; HYDROGEN CYANIDE; N BOC N,O ISOPROPYLIDENE LEVO SERINAL; PENTANOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0033597389     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00159-7     Document Type: Article

References (30)

1. 1. (a) Williams, L.; Zhang, Z.; Shao, F.; Carroll, P. J.; Joullié M. M. Tetrahedron 1996, 52, 11673-11694.
2. (b) Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697-1700.
3. (c) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439-1446.
4. (d) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293-4301.
5. 2. Gruza, H.; Kiciak, K.; Krasinski, A.; Jurczak, J, Tetrahedron: Asymmetry 1997, 8, 2627-2631.
6. 3. Imashiro, R.; Sakurai, O.; Yamashita, T.; Horikawa, H. Tetrahedron 1998, 54, 10657-10670.
7. 4. Zandbergen, P.; van der Linden, J.; Brussee, J.; van der Gen, A. Synth. Commun. 1991, 21, 1387-1391.
8. 5. Provided that the hydroxyl substituent has the highest priority.
9. 6. Zandbergen, P.; Brussee, J.; van der Gen, A.; Kruse, C. G. Tetrahedron: Asymmetry 1992, 3, 769-774.
10. 7. Hulsbos, E.; Marcus, J.; Brussee, J.; van der Gen, A. Tetrahedron: Asymmetry 1997, 8, 1061-1067.
11. 8. Warmerdam, E. G. J. C.; van Rijn, R. D.; Brussee, J.; Kruse, C. G.; van der Gen, A. Tetrahedron: Asymmetry 1996, 7, 1723-1732.
12. 9. Warmerdam, E. G. J. C.; van den Nieuwendijk, A. M. C. H.; Kruse, C. G.; Brussee, J.; van der Gen, A. Recl. Trav. Chim. Pays Bas 1996, 115, 20-24.
13. 10. (a) Kruse, C. G. In Chirality in Industry; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; John Wiley: New York, 1992; p. 279-299.
14. (b) Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555-1564.
15. (c) Brussee, J.; van der Gen, A. In Stereoselective Biocatalysis; Patel, R., Ed.; Marcel Dekker: New York, 1999; in press.
16. 11. (a) Danieli, B.; Barra, C.; Carrea, G.; Riva, S. Tetrahedron: Asymmetry 1996, 7, 1675-1682.
17. (b) Danieli, B.; Frattini, S.; Roda, C.; Carrea, G.; Riva, S. J. Mol. Cat. B, Enz. 1998, 5, 223-228.
18. 12. Brussee, J.; Loos, W. T.; Kruse, C. G.; van der Gen, A. Tetrahedron 1990, 46, 979-986.
19. 13. Personal communication, Ing. P. J. Gerrits, Leiden Institute of Chemistry, Leiden University.
20. 14. Cram, D. J.; Wilson, D. R. J. Am. Chem. Soc. 1963, 85, 1245-1249.
21. 15. (a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 18, 2199-2204.
22. (b) Anh, N. T. Top. Curr. Chem. 1980, 88, 114-162.
23. 16. (a) Andrés, J. M.; Pedrosa, R. Tetrahedron: Asymmetry 1998, 9, 2493-2498.
24. (b) Hertweck, C.; Goerls, H.; Boland, W. Chem. Commun. 1998, 1955-1956.
25. (c) Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091.
26. 17. (a) Garner, P. Tetrahedron Lett. 1984, 25, 5855-5858.
27. (b) McKillop, J.; Still, I. W. J.; Watson, R. J., Lewis, N. Synthesis 1994, 31-33.
28. (c) Dondoni, A.; Perone, D. Synthesis 1997, 527-529.
29. (d) Roush, W. R.; Hunt, J. A. J. Org. Chem. 1995, 60, 798-806.
30. 18. Marcus, J.; Brussee, J.; van der Gen, A. Eur. J. Org. Chem. 1998, 2513-2517.