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Faber, K. et al.: 2015 Science of Synthesis, 1: Biocatalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-214-00139
Biocatalysis in Organic Synthesis 1

1.3.2 Resolution of Alcohols, Amines, Acids, and Esters by Nonhydrolytic Processes

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Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.

Authors: Asano, Y.; Babich, L.; Bertau, M.; Cobucci-Ponzano, B.; Díaz-Rodríguez, A.; Engel, U.; Faber, K.; Flitsch, S. L.; Glueck, S. M.; Gotor-Fernández, V.; Green, A. P.; Hall, M.; Hartog, A. F.; Hepworth, L. J.; Hollmann, F.; Jeromin, G. E.; Lauchli, R.; Lavandera, I.; Liese, A.; Martínková, L.; Moracci, M.; Pesci, L.; Rodríguez-Mata, M.; Rozzell, D.; Rudat, J.; Schmidberger, J. W.; Servi, S.; Slomka, C.; Syldatk, C.; Tasnádi, G.; Tessaro, D.; Veselá, A. B.; Voglmeir, J.; Wever, R.

Title: Biocatalysis in Organic Synthesis 1

Print ISBN: 9783131741318; Online ISBN: 9783131975218; Book DOI: 10.1055/b-003-125815

1st edition © 2015. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

The use of hydrolases has become a conventional process in organic synthesis, not only for the preparation of optically pure compounds, but also for regio- and chemoselective processes. Their utility for selective transformations under mild reaction conditions make hydrolases attractive catalysts for performing certain transformations that are difficult to achieve by nonenzymatic strategies. Nowadays, many companies use lipases for the preparation of high-added-value compounds and pharmaceuticals because of the advantages of hydrolase-catalyzed processes, which include cost and environmental benefits. Their commercial availability, lack of cofactor dependency, and activity in both aqueous and organic media has allowed the development of asymmetric transformations which are summarized in this chapter. After a brief general introduction discussing the potential of hydrolases in organic synthesis, asymmetric reverse hydrolytic processes are analyzed, substituting the conventional hydrolase nucleophile, water, for other species such as alcohols, amines, esters, or ammonia. The kinetic resolution and dynamic kinetic resolution reactions of alcohols and amines are presented, using esters or carbonates for the production of esters, amides, and carbamates in optically active form. Finally, the resolution of carboxylic acids or esters is described via less-employed interesterification, aminolysis, and ammonolysis processes.

Key words

acylation - alcohols - alkoxycarbonylation - amines - aminolysis - ammonolysis - asymmetric synthesis - carbonates - esters - hydrolases - interesterification - kinetic resolution - lipases - transesterification
 
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