Chiral Reactions in Heterogeneous Catalysis

204 Pages·1995·12.443 MB·English

by  Georges Jannes, Vincent Dubois (auth.), Georges Jannes, Vincent Dubois (eds.)

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.
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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
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