Optically active tertiary alcohols by biocatalysis
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-1 H -inden-1-ol-(+)- 1a has been reported. [ 9 ] CAL-A (lipase-A from Candida antarctica ) was found the best...
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Taylor & Francis
2017
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| Online Access: | https://dx.doi.org/10.6084/m9.figshare.4498646.v2 https://tandf.figshare.com/articles/journal_contribution/Optically_Active_Tertiary_Alcohols_by_Biocatalysis/4498646/2 |
| Summary: | 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-1 H -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 ] |
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