Catalytic Methods in Asymmetric Synthesis (eBook)

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