Table of Contents

Foreword vii

Preface ix

Contributors xi

Abbreviations xiii

1 Catalytic Reduction of Amides Avoiding LiAlH4 or B2H6 1
Deborah L. Dodds and David J. Cole-Hamilton

2 Hydrogenation of Esters 37
Lionel A. Saudan

3 Synthesis of Chiral Amines Using Transaminases 63
Nicholas J. Turner and Matthew D. Truppo

4 Development of a Sitagliptin Transaminase 75
Jacob M. Janey

5 Direct Amide Formation Avoiding Poor Atom Economy Reagents 89
Benjamin M. Monks and Andrew Whiting

6 Industrial Applications of Boric Acid and Boronic Acid-Catalyzed Direct Amidation Reactions 111
Joanne E. Anderson, Jannine Cobb, Roman Davis, Peter J. Dunn, Russ N. Fitzgerald, and Alan J. Pettman

7 OH Activation for Nucleophilic Substitution 121
Jonathan M.J. Williams

8 Application of a Redox-Neutral Alcohol Amination in the Kilogram-Scale Synthesis of a GlyT1 Inhibitor 139
Martin A. Berliner

9 Olefin Metathesis: From Academic Concepts to Commercial Catalysts 163
Justyna Czaban, Christian Torborg, and Karol Grela

10 Challenge and Opportunity in Scaling-up Metathesis Reaction: Synthesis of Ciluprevir (BILN 2061) 215
Nathan Yee, Xudong Wei, and Chris Senanayake

11 C–H Activation of Heteroaromatics 233
Koji Hirano and Masahiro Miura

12 The Discovery of a New Pd/Cu Catalytic System for C–H Arylation and Its Applications in a Pharmaceutical Process 269
Jinkun Huang, Xiang Wang, and Johann Chan

13 Diarylprolinol Silyl Ethers: Development and Application as Organocatalysts 287
Hiroaki Gotoh and Yujiro Hayashi

14 Organocatalysis for Asymmetric Synthesis: From Lab to Factory 317
Feng Xu

15 Catalytic Variants of Phosphine Oxide-Mediated Organic Transformations 339
Stephen P. Marsden

16 Formation of C–C Bonds Via Catalytic Hydrogenation and Transfer Hydrogenation 363
Joseph Moran and Michael J. Krische

Index 409

About the Author

PETER J. DUNN, PhD, is Global Green Chemistry Lead forPfizer. Dr. Dunn has played a key role in the development ofcommercial processes to make several drugs, including Viagra ,Emselex , Revatio , and Sampatrilat. K. K. (MIMI) HII, PhD, holds a Readership in Catalysis inthe Department of Chemistry at Imperial College London. Herresearch focuses on the development of sustainable catalyticprocesses for organic synthesis. MICHAEL J. KRISCHE, PhD, is Director of the Center forGreen Chemistry and Catalysis and Robert A. Welch Chair in Scienceat The University of Texas at Austin. He is the recipient of theTetrahedron Young Investigator Award, Humboldt Prize, PresidentialGreen Chemistry Challenge Award, and ACS Elias J. Corey Award. MICHAEL T. WILLIAMS, PhD, is an independent consultant.Previously, he was an executive director at Pfizer and played a keyrole in the development and commercialization of many drugs,including Zoloft , Viagra , and Relpax .

Reviews

In brief, I have read this book with pleasure and Irecommend it to all chemists working or getting started in thefield of catalysis. (Angew. Chem. Int.Ed., 1 October 2014)