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Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis Organic Synthesis 2 DOI: 10.1055/sos-SD-215-00046
Biocatalysis in Organic Synthesis 2

2.1.3 Acyloin, Benzoin, and Related Reactions

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

Authors: Au, S. K.; Bartsch, S.; Beecher, D.; Boffi, A.; Bommarius, A. S.; Bonamore, A.; Brown, G.; Busto, E.; Clapés, P.; Faber, K.; Fischereder, E.-M.; France, S. P.; Fuchs, C. S.; Geertsema, E. M.; Glieder, A.; Gruber-Khadjawi, M.; Hall, M.; Hanefeld, U.; Hussain, S.; Ilari, A.; Janssen, D. B.; Kaluđerović, G. N.; Kroutil, W.; Lamm, A. S.; Leipold, F.; Lewin, R.; Li, A. T.; Li, Z.; Majerić Elenkov, M.; Micklefield, J.; Moody, T. S.; Mix, S.; Müller, M.; Poelarends, G. J.; Pohl, M.; Pressnitz, D.; Resch, V.; Richter, N.; Rosazza, J. P. N.; Schreckenbach, H. F.; Simon, R. C.; Steiner, K.; Szymański, W.; Thompson, M. L.; Turner, N. J.; Venkitasubramanian, P.; Vogel, A.; Wechsler, C.; Wessjohann, L. A.; Wohlgemuth, R.

Title: Biocatalysis Organic Synthesis 2

Print ISBN: 9783131741615; Online ISBN: 9783131975317; Book DOI: 10.1055/b-003-125813

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

Subjects: Organic Chemistry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

This chapter gives a broad overview of different thiamine diphosphate (ThDP) dependent enzymes and their applicability in organic synthesis as a practical alternative to traditional cross-coupling reactions. Complementary to known nonenzymatic umpolung reactions, enzymatic versions of the benzoin condensation, the asymmetric cross-benzoin condensation, the resolution of racemic 2-hydroxy ketones via C—C bond cleavage, the synthesis of bis(α-hydroxy ketones), the homocoupling of aliphatic aldehydes, the Stetter reaction, and aldehyde–ketone cross-benzoin reactions have been developed. The broad diversity of the products from enzymatic transformations is nicely complemented by the possible subsequent diversity-oriented chemistry. Starting from simple, commercially available aldehydes, many different chiral building blocks can be selectively obtained in a few steps, thus mimicking the diversity-oriented biosynthesis of natural biosynthetic pathways.

Key words

regioselectivity - enantioselectivity - enzyme catalysis - C—C bond formation - asymmetric Stetter reaction - asymmetric benzoin condensation - asymmetric enzyme catalysis - thiamine diphosphate - stereocontrol - benzoins - acyloins - chiral resolution - kinetic resolution
 
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