Page 20 - Catalysts for Fine Chemical Synthesis Vol 1 - Robert & Poignant

Catalysts for Fine Chemical Synthesis: Hydrolysis, Oxidation and Reduction. Volume 1
Edited by Stan M Roberts and Geraldine Poignant
Copyright  2002 John Wiley & Sons, Ltd.
ISBN: 0-471-98123-0

1 The Integration of
Biotransformations

into the Catalyst Portfolio

CONTENTS
1.1 Hydrolysis of esters, amides, nitriles and oxiranes . . . . . . . . . 4
1.2 Reduction reactions . . . . . . . . . . . . . . . . . . 9
1.2.1 Reduction of carbonyl compounds . . . . . . . . . . . . . 10
1.2.2 Reduction of alkenes . . . . . . . . . . . . . . . . . . 13
1.3 Oxidative transformations . . . . . . . . . . . . . . . . 17
1.4 Carbon±carbon bond-forming reactions . . . . . . . . . . . . 26
1.5 Conclusions . . . . . . . . . . . . . . . . . . . . . 37
References . . . . . . . . . . . . . . . . . . . . . . . 39

The science of biotransformations has been investigated since the days of
[1]
Pasteur . However, progress in the use of enzymes and whole cells in synthetic
organic chemistry was relatively slow until the 1950s, when the use of micro-
organisms to modify the steroid nucleus was studied in industry and academic
[2]
laboratories . Thus conversions such as the transformation of 17a-acetoxy-11-
deoxycortisol into cortisol (hydrocortisone) (1), using the microorganism

COCH 2 OH
Me
HO OH
Me

O
(1)

Curvularia lunata to introduce the 11b-hydroxy group directly, helped to revive
interest in the application of biological catalysis to problems in synthetic
organic chemistry. The momentum was continued by Charles Sih, J. Bryan
Jones, George Whitesides and others, until, by the mid-1980s, biocatalysis