Enzyme-catalyzed resolution of aromatic ring fused cyclic tertiary alcohols

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 transeste...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: Ozdemirhan, Devrim, Sezer, Serdar, Sonmez, Yasemin
Language:unknown
Published: Elsevier BV 2008
Subjects:
Physical and Theoretical Chemistry
Inorganic Chemistry
Organic Chemistry
Catalysis
Antarc*
Antarctica
Online Access:https://hdl.handle.net/11511/67050
https://doi.org/10.1016/j.tetasy.2008.12.002
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Summary: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.

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