Asymmetric amino acid synthesis: Mitsunobu reaction on chiral cyanohydrins

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 529-530

  Decicco, Carl P ^a   Grover, Paul ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002083857     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6139     Document Type: Article

References (18)

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2. (b) Coppala, G. M.; Schuster, H.F. Asymmetric Synthesis: Construction of Chiral Molecules using Amino Acids; Wiley: New York, 1987.
3. (c) Duthaler, O.R. Tetrahedron 1994, 50, 1539.
4. (d) Studer, A. Synthesis 1996, 793.
5. Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y. J. Org. Chem. 1996, 61, 440.
6. Warmerdam, E. G. J. C.; Brussee, J.; Kruse, C. G.; van der Gen, A. Phosphorous, Sulfur, Silicon Rel. Elem. 1993, 75, 3.
7. Campbell, J. A; Hart, D. J. J.Org.Chem. 1993, 58, 2900.
8. see for example (a) Reetz, M. T.; Kunish, F.; Heitman, P. Tetrahedron Lett. 1986, 27, 4721.
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11. (d) Mori, A.; Ohno, H.; Nitta, H.; Tanaka, K.; Inou, S. Synlett 1991, 563.
12. (e) Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001.
13. (f) Jiang, Y.; Zhou, X.; Wenhao, H.; Zhi, L.; Aiqiao, M. Tetrahedron Asymmetry 1995, 6, 2915.
14. (g) Schrader, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 917.
15. Huuhtanen, T. T.; Kanerva, L. T. Tetrahedron Asymmetry, 1992, 3, 1223.
16. for additional references see (a) Ognyanov, V. I.; Datcheva, V.K.; Kyler, K.S. J. Am. Chem. Soc. 1991, 113, 6993.
17. (b) Zandbergen, P.; van der Linden, J.; Brussee, J.; van der Gen, A. Syn. Comm. 1991, 21, 1387.
18. A modified procedure was recently reported using oxynitrilase from Hevea brasiliensis in which several aromatic and heteroaromatic aldehydes, including benzaldehyde and furanal, were converted to cycanohydrins in excellent chemical and optical yields.; Schmidt, M.; Herve, S.; Kiempier, N.; Griengl, H. Tetrahedron, 1996, 52, 7883.