Enantioselective synthesis of 4,5,6,7-tetrahydro-4-oxo-benzofuran-5-yl acetate and 1-benzyl-4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate using chemoenzymatic methods

Date

2007-03-01

Author

Demir, Ayhan Sıtkı
Caliskan, Zerrin
Sahin, Ertan

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The chemoenzymatic synthesis of both of the enantiomers of pharmacologically interesting compounds such as 4,5,6,7-tetrahydro-4-oxobenzofuran-5-yl acetate (2a), 4,5,6,7-tetrahydro-4-oxo-6,6-dimethylbenzofuran-5-yl acetate (2b), and their hydroxy derivatives 3a, 3b, 1-benzyl4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate (5), starting from 6,7-dihydrobenzofuran-4(5H)-one (la), 6,7-dihydro-6,6-dimethylbenzofuran4(5H)-one (7b), and 1-benzyl-6,7-dihydro-1 H-indol-4(5H)-one (4) are reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated kinetic resolution of alpha'-acetoxy enone provides acetoxy and hydroxy derivatives in good yields and high enantiomeric excesses.

Subject Keywords

Process Chemistry and Technology, Biochemistry, Bioengineering, Catalysis

URI

https://hdl.handle.net/11511/56394

Journal

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC

DOI

https://doi.org/10.1016/j.molcatb.2006.09.006

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir, Z. Caliskan, and E. Sahin, “Enantioselective synthesis of 4,5,6,7-tetrahydro-4-oxo-benzofuran-5-yl acetate and 1-benzyl-4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate using chemoenzymatic methods,” JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, pp. 87–92, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56394.