Optically active tertiary alcohols by biocatalysis

• Published in: Synthetic Communications
• Main Author: Özdemirhan, Devrim
• Other Authors: BAİBÜ, Fen Edebiyat Fakültesi, Kimya Bölümü, orcid:0000-0002-8828-0507
• Format: Article in Journal/Newspaper
• Language: English
• Published: Taylor & Francis Inc 2017
• Subjects: Alcohols; Biocatalysis; Enzyme-Catalyzed; Optically Active; Tertiary; Antarc*; Antarctica
• Online Access: https://hdl.handle.net/20.500.12491/9434; https://doi.org/10.1080/00397911.2016.1274032

WOS:000396796500001 Initially, chemoenzymatic route to optically active aromatic ring-fused cyclic tertiary alcohols (S)-(-)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol-(-)- 1b, (S)-(+)-1-methyl-2,3-dihydro-1H-inden-1-ol-(+)-1a has been reported.([9]) CAL-A (lipase-A from Candida antarctica) was found the best biocatalyst for 1b, CAL-A cross linked enzyme aggregate (CLEA) for 1a, with ee values of 20 and 45% and the esters 2b and 2a with ee values 99 and 71%. Then, cyclopent-2-ene anchored tertiary allyl 1a', homoallyl 1b' and homopropargyl 1c alcohols have been enzymaticly resolved in a high ee (up to 90%) with 44, 40, and 43% chemical yield, respectively, cyclohex-2-ene anchored tertiary allyl 3a, homoallyl 3b, and homopropargyl 3c alcohols in high ee (up to 97%) too with 42, 45, and 49% chemical yield in turn. Chiral dienes yield the spirocyclic dihydropyrans through ring-closing methathesis with 74 and 78% chemical yields with 90 and 97% ee. Chiral enynes afford the cyclopentenone pyrans through Pauson-Khand reaction with 80 and 81% chemical yields as single diastereomers as reported subsequently.([1a])