Enzyme-catalyzed resolution of aromatic ring fused cyclic tertiary alcohols

Date

2008-12-01

Author

Ozdemirhan, Devrim
Sezer, Serdar
Sonmez, Yasemin

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An efficient chemoenzymatic route for the synthesis of optically active aromatic ring fused cyclic tertiary alcohols (S)-(-)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol (-)-1b and (S)-(+)-1-methyl-2,3-dihydro-1H-inden-1-ol (+)-1a has been developed. Different lipases have been tested in the transesterification of these tertiary alcohols; CAL-A (Candida antarctica Lipase A) was found to be the best biocatalyst for 1b and CAL-A-CLEA (Lipase A, C. antarctica, cross-linked enzyme aggregate) for la, obtained with ee values of 20% and 45%, respectively, and the corresponding esters 2b and 2a with the ee values of 99% and 71%, respectively.

Subject Keywords

Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/67050

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2008.12.002

Collections

Department of Chemistry, Article

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Citation Formats

D. Ozdemirhan, S. Sezer, and Y. Sonmez, “Enzyme-catalyzed resolution of aromatic ring fused cyclic tertiary alcohols,” TETRAHEDRON-ASYMMETRY, pp. 2717–2720, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/67050.