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
Özet
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. (c) 2006 Elsevier B.V. All rights reserved.
Atıf için künye
Demir, A. S., Caliskan, Z., & Şahin, E. (2007). 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, 44, 87–92. https://doi.org/10.1016/j.molcatb.2006.09.006
BibTeX
@article{demir2007-66619,
author = {Demir, Ayhan S. and Caliskan, Zerrin and Şahin, Ertan},
title = {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 = {JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC},
year = {2007},
volume = {44},
pages = {87--92},
issn = {1381-1177},
doi = {10.1016/j.molcatb.2006.09.006},
url = {https://akademik.atauni.edu.tr/yayinlar/66619-enantioselective-synthesis-of-4567-tetrahydro-4-oxo-benzofuran-5-yl-acetate-and}
}