Chiral Reactions in Heterogeneous Catalysis PDF
Preview Chiral Reactions in Heterogeneous Catalysis
Chiral Reactions in Heterogeneous Catalysis Chiral Reactions in Heterogeneous Catalysis Edited by Georges Jannes and Vincent Dubois CER1A / Meurice Institute Brussels, Belgium Springer Science+Business Media, LLC Library of Congress Cataloging-in-Publication Data On file Proceedings of the First European Symposium on Chiral Reactions in Heterogeneous Catalysis, held October 25-26, 1993, in Brussels, Belgium ISBN 978-1-4613-5780-3 ISBN 978-1-4615-1909-6 (eBook) DOI 10.1007/978-1-4615-1909-6 © 1995 Springer Science+Business Media New York Originally published by Plenum Press, New York in 1995 Softcover reprint of the hardcover 1st edition 10 9 8 76 5 4 3 2 1 All rights reserved No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher ORGANIZINGCOMMITTEE A. Baukens V. Dubois G. Jannes J.P. Puttemans P. VandeIWegen SCIENTIFICCOMMITTEEOFTHECENTENARY Prof]. Vandegans, chairman Prof A. Blondeel, treasurer Prof A. Debourg Prof P. Dysseler Prof G. Jannes Prof J. Hanuise Prof T. Lepoint Prof c.A. Masschelein Dr. J.P. Simon v PREFACE It was a great honor for us to organize ChiCat, a symposium devoted to Chiral ReactionsinHeterogeneousCatalysisandtobethehostsofmorethan 120scientistscoming from everywhere in the industrialized world, to celebrate together one century ofexistence ofInstitutMeurice. Thisschoolwasestablishedin 1892whenan industrialchemist,named Albert Meurice, decidedto educatepracticalchemistsaccording totheperceivedneedsofthe industryofthat time. Thisisexactlywhat we arestill trying to do. Itis the reason why, thirty years ago, we started aresearch activity incatalysis, and why we progressively devote this research to the applications ofcatalysis in the field offine chemicals. In this respect, we are very close to another initiative of Albert Meurice, who started the first production of synthetic pharmaceuticalsinBelgiumduringWorld WarI. Thisbusiness lateronbecameapartofthe BelgiancorporationDCB,stillveryactiveinpharmaceuticalstoday. Theschoolcreated byAlbert Meuricemerged in thefifties with anotherschool thathad been created to meet the same needs in the field of the food industries, mainly distilleries and breweries. This merger was done in the frame of the establishment of CERIA. For peopleincatalysis,ceriastands forcerium oxide, but for those who engineered the concept, CERIAstood for Center ofEducation and Research for the Food and Chemical Industries. Our center was created to stimulate the rebuilding of these industries in the province of Brabant, ruined by the war. Today it plays a prominent role in the development of technopoles in the new region ofBrussels organized in federal Belgium. This explains the financial support we received from Brussels Ministry of Economy for the Centenary of InstitutMeurice. However, this symposium is probably the last meeting of the old fashioned Contact Group - Catalysis as supported by the National Science Foundation. The structure of financial supporttoscientificresearchhasalso beenmodified. We hopethat itwill not result in further diminishing the contribution of the national and local governments to the necessaryendeavorofBelgium inresearchanddevelopment. Twenty years ago, the Societe Royale de Chimie founded its Catalysis Division. The first presidentofthis Division, ProfessorDelmon, accepted that the first eventorganized by the division should help celebrate the twenty-fifth anniversary ofCERIA: it was the First International Symposium on the Relations between Homogeneous and Heterogeneous Catalytic Phenomena, aseries that is still going on. Nowadays, for the centenary ofInstitut Meurice, we are pleased to organize this meeting in the frame ofthe Catalysis Division of the Societe Royale de Chimie. It is good to have some traditional friends when celebrating anniversaries. A newcomer in the Belgian Catalysis community is the Catalysis Committee of the Royal Belgian Academy Council ofApplied Sciences. This Committee has issued a report vii on Modern Catalysis that has received positive echoes in Japan as well as in the United States : we hope that it will not remain without answer in Belgium. The Royal Academy Councilhasacceptedto giveitspatronagetooursymposium; itisagreathonor,andweare thankfulfor this. Finally, Iwould like to acknowledge the fantastic work done by my co-workers and to publicly thank them. I am proud to have them as co-workers and friends. Vincent Dubois did ahuge part ofthe long term organization, sacrificingmore than six months ofhis Ph.D. research to prepare this event. Anne Baukens, Danielle Philip, Maryse Talbot, Pascal Vanderwegen and Jean-Pierre Puttemans also devoted time and energy to make attendance as effective and pleasant as possible. Thanks are finally due to the staffofour Institute, to the ScientificCommitteeofthe Centenary, and to somecolleagues in ourCenter, especially in thehotelschool. GeorgesJannes viii ACKNOWLEDGMENTS Thefollowing companiesagreed to providefinancial supportto the symposium: Amer-Sil CatalystsandChemicalsEurope FinaResearch Hewlett-Packard Janssen Pharmaceutica Johnson-Matthey SanofiPharma Solvay UCB vanLerberghe Thesymposiumwasalso supportedby : FNRS-NFWO(Belgium'sNational ScienceFoundations) Ministerede l'Economiede laRegion deBruxelles-Capitale Thefollowing companiesparticipatedinthe permanentexhibition : Analis(Parr) AutoclaveEngineers JanssenChimica Micromeritics Sigma-Aldrich TechnologyCatalysts Theorganizersaregrateful to themfortheirgenerosity. ix CONTENTS Introduction . . 1 THE PLACEOFHETEROGENEOUSCATALYSISINTHECHIRALITYFIELD Commercial Outlookfor Chirality. Quo Vadis? . . 5 E. Polastro Strategiesfor Asymmetric Synthesis. WhatistheRoleofHeterogeneousCatalysis? 21 L. Ghosez HomogeneousEnantioselectiveCatalysis 29 H. Brunner ScopeandLimitationsofthe ApplicationofHeterogeneousEnantioselective Catalysis........ 33 no. BlaserandB. Pugin HYDROGENAnON SYSTEMS: TOWARDABETTERUNDERSTANDING ModificationofSupported andUnsupportedNickel Catalystsbya-Amino anda- Hydroxy Acidsfor ChiralReactions. . 61 G. Webb Enantio-DifferentiatingHydrogenationofSimpleAlkanoneswith Asymmetrically ModifiedHeterogeneousCatalyst....... 75 T. Osawa, A. Tai, Y. Imashiand S. Takasaki Enantio-DifferentiatingHydrogenationof2-Butanone :DistinctionbetweenCH 3 and CzHswithaModifiedNickelCatalyst... 83 T. Haradaand T. Osawa xi ChiralHydrogenationofEstroneandEstrone-3-MethylEther 89 Gy. Gondos, Gy. Wittmann,M. BartokandJ.c. Orr EnantioselectiveHydrogenationofa-Ketoesters : A MolecularViewonthe Enantio-Differentiation 95 A. Baiker, T. Mallat, B. Minder, O. Schwalm,K.E. Simonsand1. Weber StudiesonthePlatinumCinchonaAlkaloid CatalystforEnantioselectivea- KetoesterHydrogenation................. 105 PJ. Collier, T. Goulding, 1.A. Iggoand R Whyman AsymmetricHydrogenationofEthylPyruvateUsingPt-ContainingZeolites Modifiedwith(-)-Cinchonidine III W. Reschetilowski, U. Bohmerand J. Wiehl HYDROGENAnON SYSTEMS: BROADENINGTHE SCOPE HeterogeneousCatalyticReactionsUsingChiral Auxiliariesand Producing EnantiomersinExcess 121 A. Tungler, T. Tarnai, T. Mathe, J. PetroandR.A. Sheldon EnzymaticResolutionofBiologicallyActivePrecursorsversus Asymmetric InductioninHeterogeneousCatalysis........... .. 135 H. Honig, R Rogi-Kohlenprathand H. Weber Enantio-and DiastereoselectiveReductionofDisubstitutedAromatics 141 K. Nasar, M. Besson, P. Gallezot, F. FacheandM. Lemaire HeterogeneousAsymmetricCatalysiswithC SymmetricAmine-Modified 2 Rhodium/Silica... .. 147 P. Gamez, F. Fache, M. LemaireandP Mangeney AnInvestigationoftheModeofHydrogen Additionin Stereoselective HeterogeneousCatalyticHydrogenations......... .. 151 A. Tungler, T. Tarnai, T.Mathe, G. Toth, J. Petroand RA. Sheldon HeterogeneousEnantioselectiveHydrogenationand DihydroxylationofCarbon- CarbonDoubleBondMediated byTransitionMetal AsymmetricCatalysts 155 D. Pini, A. Petri, A. Mastantuono and P. Salvadori xii MORE ADVANCED REACTIONS ChiralDioxo-Molybdenum ComplexesAnchored to Modified USY-Zeolites. Applicationto SelectiveEpoxidationofOlefins.. . 179 A. Corma, M. Iglesias, lR ObispoandF. Sanchez EffectofSulfoxideLoadingonthe Selectivityand ActivityofZeoliteYfor DehydrationReactions........... . 191 D. Bethell, S Feast, GJ. Hutchings, F. King, PCB Pageand SP. Saberi NovelChiralRuthenium-bis(oxazolinyl)pyridineand bis(oxazolinyl)bipyridine Complexes: AsymmetricCyclopropanationofStyrenewithDiazoacetates 197 H. Nishiyama, H. Matsumoto, S.B ParkandK Itoh Polymer SupportedN-A1kylnorephedrinesas HighlyEnantioselectiveChiral Catalystsfor the AdditionofDialkylzincs to Aldehydes. . 203 K Soai and M. Watanabe AuthorIndex. ......209 SubjectIndex 211 xiii
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