Chemoenzymatic Sequential Catalysis with Carbonic Anhydrase for the Synthesis of Chiral Alcohols from Alkanes, Alkenes, and Alkynes

Abstract

Chiral alcohols are important intermediates for various fine chemicals and pharmaceuticals. Integrating chemical catalysis and efficient enzyme catalysis in sequential systems for the synthesis of chiral alcohols is considered an ecofriendly and promising approach. Herein, employing a highly selective carbonic anhydrase II and different chemical catalysts, we constructed three general chemoenzymatic sequential systems for chiral alcohol compound synthesis from alkanes, alkenes, and alkynes, respectively. Compared to classical approaches, the combination of chemical catalysis and promiscuous carbonic anhydrase catalysis is simple and efficient since it requires only mild reaction conditions and avoids expensive chiral ligands and cumbersome operation steps. In this integrated approach, a wide variety of readily available aryl alkanes, alkenes, and alkynes are transformed into valuable chiral alcohols with excellent enantioselectivity of up to 99% (nearly all above 90%). This unified strategy of combining enzymatic and chemical catalyses advances the general chemoenzymatic process for powerful and important chemical transformations.