Biosynthesis of chiral cyclic and heterocyclic alcohols via CO/C–H/C–O asymmetric reactions

Catalysis Science & Technology Pub Date: 2021-03-04 DOI: 10.1039/D1CY00113B

Abstract

Chiral cyclic and heterocyclic alcohols are important structural units for fine chemicals, agrochemicals, and chiral pharmaceuticals such as ladostigil, imbruvica, and sulopenem. Natural enzymes show low affinity toward molecules harboring bulky substituents or similarly-sized substituents on the ring. Thus, engineered enzymes represent an alternative option for the biosynthesis of chiral cyclic and heterocyclic alcohols. This review covers the recent progress in various biological approaches applied to the synthesis of enantiomerically pure cyclic and heterocyclic alcohols, including enzymatic asymmetric reduction of the C[double bond, length as m-dash]O bond, asymmetric hydroxylation of the C–H bond, and asymmetric hydrolysis reaction of the C–O bond. This review gathers relevant theoretical and experimental clues for organic synthesis of chiral cyclic and heterocyclic alcohols.

Graphical abstract: Biosynthesis of chiral cyclic and heterocyclic alcohols via C [[double bond, length as m-dash]] O/C–H/C–O asymmetric reactions
Recommended Literature