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High‐Throughput Preparation of Optically Active Cyanohydrins Mediated by Lipases
Author(s) -
Thomas Juliana Christina,
Aggio Bruno Bernardi,
Marques de Oliveira Alfredo Ricardo,
Piovan Leandro
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601028
Subject(s) - cyanohydrin , chemistry , kinetic resolution , flow chemistry , context (archaeology) , acylation , optically active , enantiomer , enantiomeric excess , combinatorial chemistry , lipase , organic chemistry , enantioselective synthesis , catalysis , enzyme , paleontology , biology
Cyanohydrins are versatile compounds with high applicability in organic synthesis; they are used as starting materials for the synthesis of other chemical targets with high industrial added value. Lipase‐mediated kinetic resolution reactions are a promising route for the synthesis of optically active cyanohydrins. These reactions can be carried out through the acylation of cyanohydrins or the deacylation of cyanohydrin esters, with different biocatalysts and under different reaction conditions. Unfortunately, depending on the substrate structure, long reaction times can be required to achieve suitable enantiomeric excesses. In this context, we present a high‐throughput protocol for the production of optically active cyanohydrins in continuous‐flow mode. The products were obtained with moderate to good enantioselectivity ( E values from 8 up to >200) and with productivity values from 2.4 to 8.7 times higher in continuous‐flow mode than in batch mode. Moreover, the reaction times were reduced from hours in batch mode to minutes in continuous‐flow mode.