Secondary alcohol irreversible lipase-catalyzed transesterifications

Kinetic Resolution by Transesterification. Asymmetric transformation involving acylation of chiral alcohols is by far the most common example of kinetic resolution by lipase-catalyzed transesterification, most commonly with irreversible vinyl esters. This field is now becoming the most widely applied technique involving lipases. Recent reports of the numerous secondary alcohol substrates include various monocyclic (eq 6) andacyclic compounds, cyanohydrins, sulfones, and glycals, to name a few. 

Lipase-Catalyzed Irreversible Transesterification of Secondary Alcohols... 

Special attention should be devoted to less conventional applications of the enzymatic transesterification methodology such as resolution of unstable substrates as racemic secondary hydroperoxides [291]. The development of new reactions in the presence of enzymes should pursued, as, for example, the simultaneous formation of a hemithioac-etal and die irreversible transesterification in the presence of a lipase [292]. Also, for synthetic applications, the combination of enzymatic and chemical asymmetrical methods could lead to interesting results, such as the one-pot lipase-catalyzed acylation and the Mitsonobu inversion of the configuration of the unreacted alcohol, which should lead to only one enantiomeric ester [293]. 

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See also in sourсe #XX -- [ , , , , , ]

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