Enantio and diastereoselectivity of cyclohexanone monooxygenase catalyzed oxidation of 1,3-dithioacetals

Tetrahedron Asymmetry

Volumn 7, Issue 2, 1996, Pages 565-570

  Colonna, Stefano ^a   Gaggero, Nicoletta ^a   Carrea, Giacomo ^a   Pasta, Piero ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE; UNSPECIFIC MONOOXYGENASE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENZYME ACTIVITY; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030020776     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00040-7     Document Type: Article

References (23)

1. Donogue, N.A.; Norris, D.B.; Trudgill, P.W. Eur. J. Biochem. 1976, 87, 175.
2. Branchaud, B.P.; Walsh, C.T. J. Am. Chem. Soc. 1985, 107, 2153.
3. Colonna, S.; Gaggero, N.; Bertinotti, A.; Carrea, G.; Pasta, P.; Bernardi, A. J. Chem. Soc.,Chem. Commun. 1995, 1123.
4. S = ratio of the rates of formation of (R) and (S)-sulfoxides.
5. E = enantiomeric ratio (Chen, C.S.; Fujimoto, Y.; Girdaukas, Y.G.; Sih, C.J. J. Am. Chem. Soc. 1982, 104, 7294).
6. Carrea, G.; Redigolo, B.; Riva, S.; Colonna, S.; Gaggero, N.; Battistel, E.; Bianchi, D. Tetrahedron: Asymmetry 1992,3, 1063.
7. Auret, B.J.; Boyd, D.R.; Cassidy, E.S.; Hamilton, R. Turley, F. Drake, A.F. J. Chem. Soc. Perkin Trans. I 1985, 1547.
8. a) Page, P.C.B.; Namwindwa, E.S. Syn Lett. 1991, 80 and references therein.
9. b) Page, P.C.B.; Wilkes, R.D.; Witty, M.G. Org. Prep. Proced. Int. 1994, 26, 702.
10. c) Page P.C.B.; Heer, J.P.; Bethell, D.; Collington, E.W.; Andrews, D.M. Syn Lett. 1995, 773.
11. Carlson, R.M.; Helquist, P.M. J. Org. Chem. 1968, 33, 2596.
12. Van Acker, L.; Anteunis, M. Tetrahedron Lett. 1974, 2, 225.
13. Holland, H.L.; Munoz, B. Can. J. Chem. 1988, 66, 2299.
14. Cashman, J.R.; Olsen, L.D. Mol. Pharmacol. 1990, 38, 573.
15. Cashman, J.R.; Olsen, L.D.; Bornheim, L.M. J. Am. Chem. Soc. 1990, 112, 3191.
16. Cashman, J.R.; Olsen, L.D.; Boyd, D.R.; McMordie, R. Austin S.; Dunlop, R.; Dalton, H. J. Am. Chem. Soc. 1992, 114, 8772.
17. Auret, B.J.; Boyd, D.R.; Dunlop, R.; Drake, A.F. J. Chem. Soc. Perkin Trans. I 1988, 2827.
18. Di Furia, F.; Licini, G.; Modena, G. Gazz. Chim. Ital. 1990, 120, 165.
19. Bortolini, O.; Di Furia, F.; Licini, G.; Modena, G.; Rossi, M. Tetrahedron Lett. 1986, 27, 6257.
20. Rettie, A.E.; Bogucki, B.D.; Lim, I.; Meier, G.P. Mol. Pharmacol. 1990, 37, 643.
21. Hoppmann, A.; Weyersthal, P.; Zummack, W. Liebigs Ann. Chem. 1977, 1547.
22. Boyd, D.R.; Sharma, N.D.; Dorman, J.H.; Dunlop, R.; Malone, J.F.; McMordie, R. Austin S.; Drake, A.F. J. Chem. Soc. Perkin Trans. I 1992, 1105.
23. Page, P.C. Bulman; Garey, M.T.; Porter, R.A. Tetrahedron: Asymmetry 1993, 4, 2139.