Catalytic Methods in Asymmetric Synthesis

MICHELANGELO GRUTTADAURIA is Full Professor of Organic Chemistry at the University of Palermo. His fields of interest have previously included heterocycle synthesis, physical organic chemistry, and stereoselective synthesis using organoselenium chemistry. His current interests include organocatalysis and new supported recyclable catalysts. Dr. Gruttadauria is the author of over eighty papers and reviews. FRANCESCO GIACALONE, PhD, is a Researcher in the Organic Chemistry Department at the University of Palermo. He is author or coauthor of about forty scientific papers, including four reviews in peer-reviewed journals, as well as fifteen book chapters and forty congress presentations. His current research interests focus on the preparation of recyclable materials in heterogeneous catalysis for organic synthesis. In addition, Dr. Giacalone coedited the book Fullerene-Polymers: Synthesis, Properties and Applications, published by Wiley.

PREFACE xi FOREWORD xiii

CONTRIBUTORS xv

I NEW MATERIALS AND TECHNOLOGIES: SUPPORTED CATALYSTS, SUPPORTS, SELFSUPPORTED CATALYSTS, CHIRAL IONIC LIQUID, SUPERCRITICAL FLUIDS, FLOW REACTORS, AND MICROWAVES 1

1 RECYCLABLE STEREOSELECTIVE CATALYSTS 3
Carlos M. Monteiro, Alexandre F. Trindade, Pedro M. P. Gois, and Carlos A. M. Afonso

2 RECYCLABLE ORGANOCATALYSTS IN ASYMMETRIC REACTIONS 83
Michelangelo Gruttadauria, Francesco Giacalone, and Renato Noto

3 SYNTHESIS AND CHARACTERIZATION OF SUPPORTED CHIRAL CATALYSTS 177
Carmela Aprile, Hermenegildo Garcia, and Paolo P. Pescarmona

4 SYNTHESIS OF CHIRAL CATALYSTS SUPPORTED ON ORGANIC POLYMERS 209
Tor Erik Kristensen and Tore Hansen

5 SELF-SUPPORTED CHIRAL CATALYSTS 257
Hongchao Guo and Kuiling Ding

6 CATALYSIS WITH CHIRALLY MODIFIED METAL SURFACES: SCOPE AND MECHANISMS 291
Angelo Vargas, Cecilia Mondelli, and Alfons Baiker

7 CHIRAL IONIC LIQUIDS FOR ASYMMETRIC REACTIONS 323
Annie-Claude Gaumont, Yves Génisson, Frédéric Guillen, Viacheslav Zgonnik, and Jean-Christophe Plaquevent

8 ASYMMETRIC REACTIONS IN FLOW REACTORS 345
Munawwer Rasheed, Simon C. Elmore, and Thomas Wirth

9 ASYMMETRIC CATALYTIC SYNTHESIS IN SUPERCRITICAL FLUIDS 373
Tomoko Matsuda

10 MICROWAVE-ASSISTED TRANSITION METAL-CATALYZED ASYMMETRIC SYNTHESIS 391
Luke R. Odell and Mats Larhed

II RECENT ADVANCES IN ORGANOCATALYTIC, ENZYMATIC, AND METAL-BASED MEDIATED ASYMMETRIC SYNTHESIS 413

11 RECENT ADVANCES ON STEREOSELECTIVE ORGANOCATALYTIC REACTIONS. ORGANOCATALYTIC SYNTHESIS OF NATURAL PRODUCTS AND DRUGS 415
Monika Raj and Vinod K. Singh

12 RECENT ADVANCES IN BIOCATALYSIS APPLIED TO ORGANIC SYNTHESIS 491
Gonzalo De Gonzalo, Iván Lavandera, and Vicente Gotor

13 PEPTIDES FOR ASYMMETRIC CATALYSIS 529
Matthias Freund and Svetlana B. Tsogoeva

14 SILICATE-MEDIATED STEREOSELECTIVE REACTIONS CATALYZED BY CHIRAL LEWIS BASES 579
Maurizio Benaglia, Stefania Guizzetti, and Sergio Rossi

15 RECENT ADVANCES IN THE METAL-CATALYZED STEREOSELECTIVE SYNTHESIS OF BIOLOGICALLY ACTIVE MOLECULES 625
Catalina Ferrer, Xavier Verdaguer, and Antoni Riera

16 STEREOSELECTIVE NITROGEN HETEROCYCLE SYNTHESIS MEDIATED BY CHIRAL METAL CATALYSTS 671
Sherry R. Chemler

INDEX 689