Thermal and photoinduced reduction of ethyl (Z)-α-cyano-β-bromomethylcinnamate by 1-benzyl-1,4-dihydronicotinamide

Abstract

Thermal and photoinduced reduction of ethyl (Z)-α-cyano-β-bromomethylcinnamate (1) by coenzyme NAD(P)H model 1-benzyl-1,4-dihydronicotinamide (BNAH, 2) gives ethyl (E)-1-cyano-2-phenylcyclopropane-1-carboxylate (3) in the former case, and the (E)-4 and (Z)-5 isomers of ethyl α-cyano-β-methylcinnamate with the (E)-isomer as the major product in the latter case. The results are rationalized in terms of direct hydride transfer and electron transfer–debromination–hydrogen abstraction mechanism, respectively.

References

1. (a) C. Walsh, Enzymatic Reaction Mechanism, W. H. Freeman, San Francisco, 1979, p. 10; (b) I. Stryer, Biochemistry, W. H. Freeman, New York, 3rd edn., 1988, ch. 17; (c) F. H. Westheimer, in Pyridine Nucleotide Coenzyme, eds. D. Dolphin, R. Poulson and O. Avramovic, Wiley-Interscience, New York, 1988, Part A, p. 253.
2. (a) C. I. F. Watt, Adv. Phys. Org. Chem., 1988, 24, 57; (b) C. A. Coleman, J. G. Rose and C. J. Murray, J. Am. Chem. Soc., 1992, 114, 9755; (c) Y. Kim, D. G. Truhlar and M. M. Kreevoy, J. Am. Chem. Soc., 1991, 113, 7837; (d) N. Ono, R. Tamura and A. Kaji, J. Am. Chem. Soc., 1983, 105, 4017; (e) M. Goota, Y. Mikata and A. Ohno, Bull. Chem. Soc. Jpn., 1990, 63, 2683.
3. (a) G.-X. He, A. Blasko and T. C. Briuce, Bioorg. Chem., 1993, 21, 423; (b) L. P. Olson and T. C. Bruice, Biochemistry, 1995, 34, 7335; (c) O. Almarsson, E. Gopinath and T. C. Bruice, J. Am. Chem. Soc., 1993, 115, 7093.
4. (a) M. F. Powell and T. C. Bruice, J. Am. Chem. Soc., 1982, 104, 5834; 1983, 105, 1014; (b) J. W. Verhoeven, W. van Gerresheim, F. M. Martiens and S. M. van der Kerk, Tetrahedron, 1986, 42, 975; (c) L. L. Miller and J. R. Valentine, J. Am. Chem. Soc., 1988, 110, 3982; (d) B. W. Carlson and L. L. Miller, J. Am. Chem. Soc., 1985, 107, 479; (e) D. Ostovic, R. M. G. Roberts and M. M. Kreevoy, J. Am. Chem. Soc., 1983, 105, 7629; (f) D. Ostovic, J. S. Lee, R. M. G. Roberts and M. M. Kreevoy, J. Org. Chem., 1985, 50, 4206; (g) L. W. Bunting and S. Sindhuatmadja, J. Org. Chem., 1981, 46, 4211.
5. (a) S. Fukuzumi and T. Tanaka, in Photoinduced Electron Transfer, eds. M. Fox and M. Chanon, Elsevier, Amsterdam, 1988, ch. 4–10; (b) S. Fukuzumi, S. Mochizuki and T. Tanaka, J. Phys. Chem., 1990, 94, 722; (c) H.-J. Xu, G. Deng and Q. Yu, J. Chem. Soc., Chem. Commun., 1987, 916.
6. Y. C. Liu, B. Li and Q. X. Guo, Tetrahedron Lett., 1994, 35, 8429; Tetrahedron, 1995, 9671.
7. B. Li, Y. C. Liu and Q. X. Guo, J. Photochem. Photobiol. A: Chemistry, 1997, 103, 101.
8. E. W. Yankee, B. Spencer, N. E. Howe and D. J. Cram, J. Am. Chem. Soc., 1973, 95, 4220.
9. S. Kukuzumi, K. Hironaka and T. Tanaka, Chem. Lett., 1982, 1583; J. Am. Chem. Soc., 1983, 105, 4722.
10. (a) D. D. Tanner, K. Singh, A. Kharrat and A. R. Stein, J. Org. Chem., 1987, 52, 2142; (b) D. D. Tanner and A. R. Stein, J. Org. Chem., 1988, 53, 1642.
11. S. Fukuzumi, S. Mochizuki and T. Tanaka, Chem. Lett., 1988, 1983; J. Chem. Soc., Perkin Trans. 2, 1989, 1583.
12. M. J. Perkins, Radical Chemistry, Ellis Horwood, New York, London, 1994, p. 65.
13. A. C. Anderson and G. Berkelnammer, J. Am. Chem. Soc., 1958, 80, 992.
14. W. S. Caughey and K. A. Schellenberg, J. Org. Chem., 1966, 31, 1978.
15. W. Lehnert, Tetrahedron, 1973, 29, 635.