Chemoenzymatic Synthesis of 2-Bromo-6-Hydroxy-3-Methoxy-2-Cyclohexen-1-one
A chemoenzymatic synthesis of 2-bromo-6-hydroxy-3-methoxy-2- cyclohexen-1-one starting from cyclohexane-1,3-dione is reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of a'-acetoxy enone affords hydroxy-enone 5 and acetoxy enone 4 with high enantiomeric excesses in good yields.
Chemoenzymatic Synthesis of 2-Bromo-6-Hydroxy-3-Methoxy-2-Cyclohexen-1-one
A chemoenzymatic synthesis of 2-bromo-6-hydroxy-3-methoxy-2- cyclohexen-1-one starting from cyclohexane-1,3-dione is reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of a'-acetoxy enone affords hydroxy-enone 5 and acetoxy enone 4 with high enantiomeric excesses in good yields.
___
- J. Wang and T.R.R. Pettus, Tetrahedron Lett. 45, 5895-99 (2004).
- X. Xu and Y. Zhu, Tetrahedron Lett. 50, 9173-76 (1995).
- G. Liu and Z. Wang, Chem. Commun. 1129-30 (1999).
- R. Noyori and M. Suzuki, Angew. Chem., Int. Ed. Engl. 123, 847-76 (1984).
- P.W. Collins and S.W. Djuric, Chem. Rev. 93, 1533-64 (1993).
- P.P.M.A. Dols, A.J.H. Klunder and B. Zwanenburg, Tetrahedron 50, 8515-38 (1994).
- F.A. Davies and B.C. Chen, Chem. Rev. 92, 919-34 (1992).
- L. Canonica, A. Corbella, G. Jommi, F. Pelizzoni and C. Scolastico, Tetrahedron Lett. 26, 3031-34 (1966).
- M.E. Ochoa, M.S. Arias, R. Aguilar, F. Delgado and J. Tamariz, Tetrahedron 55, 14535-46 (1999).
- A.G. Csaky, M. Mba and J. Plumet, J. Org. Chem. 66, 9026-29 (2001).
- D. Lola, S. Belakovs, M. Gavars, I. Turovskis and A. Kemme, Tetrahedron 54, 1589-600 (1998).
- A. Scettri, G. Piancatelli, M. D’auria and G. David, Tetrahedron 35, 135-38 (1979).
- V. Schapiro, G. Cavalli, G.A. Seoane, R. Faccio and A.W. Mombru, Tetrahedron: Asym. 13, 2453-59 (2002).
- A.S. Demir, C. Tanyeli, H. Akg¨un , Z. C¸ alı¸skanand E. ¨Ozg¨ul, Bull. Soc. Chim. Fr. 132, 423-27 (1995).
- A.S. Demir, N. C¸ amkerten , Z. Ger¸cek, N. Duygu, O. Reis and E. Arıkan, Tetrahedron 55, 2441-48 (1999).
- A.S. Demir, H. Hamamci, F. Doganel and E. Ozgul, J. Mol. Catal. B: Enzym 9, 157-61 (2000).
- A.S. Demir, H. Hamamci, O. Sesenoglu, F. Aydogan, D. Capanoglu and R. Neslihanoglu, Tetrahedron: Asym. 12, 1953-56 (2001).
- A.S. Demir and O. Sesenoglu, Org. Lett. 4, 2021-23 (2002).
- A.S. Demir and O. Sesenoglu, Tetrahedron: Asym. 13, 667-70 (2002).
- A.S. Demir, H. Fındık and E. K¨ose, Tetrahedron: Asym. 15, 777-81 (2004).
- A. Clerici, N. Pastori and O. Porta, Tetrahedron 57, 217-25 (2001).
- R.G. Shepherd and A.C. White, J. Chem. Soc. Perkin Trans I, 2153-55 (1987).