Selectivities in Lewis Acid Promoted Reactions

325 Pages·1989·10.28 MB·English

by  Larry E. Overman (auth.)

Selectivities in Lewis Acid Promoted Reactions
NATO ASI Series
Advanced Science Institutes Series
A Series presenting the results of activities sponsored by the NA TO Science Committee,
which aims at the dissemination of advanced scientific and technological knowledge,
with a view to strengthening links between scientific communities.
The Series is published by an international board of publishers in conjunction with the
NATO Scientific Affairs Division
A Life Sciences Plenum Publishing Corporation
B Physics London and New York
C Mathematical Kluwer Academic Publishers
and Physical Sciences Dordrecht, Boston and London
o
Behavioural and Social Sciences
E Applied Sciences
F Computer and Systems Sciences Springer-Verlag
G Ecological Sciences Berlin, Heidelberg, New York, London,
H Cell Biology Paris and Tokyo
Series C: Mathematical and Physical Sciences -Vol. 289
Selectivities in Lewis
Acid Promoted Reactions
edited by
Dieter Schinzer
Institut fOr Organische Chemie,
Universitat Gi:ittingen,
Gi:ittingen, F.R.G.
Kluwer Academic Publishers
Dordrecht / Boston / London
Published in cooperation with NATO Scientific Affairs Division
Proceedings of the NATO Advanced Research Workshop on
Selectivities in Lewis Acid Promoted Reactions
Glyfada-Athens, Greece
October 2-7,1988
Library of Congress Cataloging in Publication Data
Selectivities in Lewis acid promoted reactions / edited by Dieter
Schinzer.
p. cm. -- (NATO ASI series. Series C, Mathematical and
physical sciences; v. 289)
"Proceedings of the NATO Advanced Research Workshop held in Athens
-Glyfada, Greece, October 2-7, 1988."
1. Chemical reactions, Conditions and laws of--Congresses.
2. Organic compounds--Synthesis--Congresses. 3. Lewis acids-
-Congresses. I. Schinzer, Dieter. II. Series.
0050 I . S43 1989
541.3' 92--dc20 89-19902
ISBN-13: 978-94-010-7611-1 e-ISBN-13: 978-94-009-2464-2
DOl: 10.1007/978-94-009-2464-2
Published by Kluwer Academic Publishers,
P.O. Box 17, 3300 AA Dordrecht, The Netherlands.
Kluwer Academic Publishers incorporates the publishing programmes of
D. Reidel, Martinus Nijhoff, Dr W. Junk and MTP Press.
Sold and distributed in the U.S.A. and Canada
by Kluwer Academic Publishers,
101 Philip Drive, Norwell, MA 02061, U.S.A.
In all other countries, sold and distributed
by Kluwer Academic Publishers Group,
P.O. Box 322, 3300 AH Dordrecht, The Netherlands.
Printed on acid free paper
All Rights Reserved
© 1989 by Kluwer Academic Publishers
Softcover reprint of the hardcover 1s t edition 1989
No part of the material protected by this copyright notice may be reproduced or
utilized in any form or by any means, electronic or mechanical, including photo
copying, recording or by any information storage and retrieval system, without written
permission from the copyright owner.
This book contains the proceedings of a NATO Advanced Research Workshop held within the programme
of activities of the NATO Special Programme on Selective Activation of Molecules running from 1983 to
1988 as part of the activities of the NATO Science Committee.
Other books previously published as a result of the activities of the Special Programme are:
BOSNICH, B. (Ed.) -Asymmetric Catalysis (E103), 1986
PELIZETTI, E. and SERPONE, N. (Eds.) -Homogeneous and Heterogeneous Photocatalysis (CI74) 1986
SCHNEIDER, M. P. (Ed.) -Enzymes as Catalysts in Organic Synthesis (C178) 1986
SErrON, R. (Ed.) -Chemical Reactions in Organic and Inorganic Constrained Systems (CI65) 1986
VIEHE, H. G., JANOUSEK, Z. and MERENYI, R. (Eds.) -Substituent Effects in Radical Chemistry (C189)
1986
BALZANl, V. (Ed.) -Supramolecular Photochemistry (C214) 1987
FONTANlLLE, M. and GUYOT, A. (Eds.) - Recent Advances in Mechanistic and Synthetic Aspects of
Polymerization (C215) 1987
LAINE, R. M. (Ed.) -Transformation of Organometallics into Common and Exotic Materials: Design and
Activation (E141) 1988
BASSET, J. M., et al. (Eds.) - Surface Organometallic Chemistry: Molecular Approaches to Surface
Catalysis (C231) 1988
WHITEHEAD, J. c. (Ed.) -Selectivity in Chemical Reactions (C245) 1988
CHANON, M., JULLIARD, M. and POITE, J. C. (Eds.) -Paramagnetic Organometallic Species in Activa
tion/Selectivity, Catalysis (C257) 1988
MlNISCI, F. (Ed.) -Free Radicals in Synthesis and Biology (C260) 1989
SCHUBERT, U. (Ed.) -Advances in Metal Carbene Chemistry (C269) 1989
TABLE OF CONTENTS
Foreword vii
List of Participants ix
Chapter 1: L.E. Overman: "Cationic Cyclization Reactions Terminated by Pinacol Rearrangements" 1
Chapter 2: H. Mayr: "Control of Electrophilicity in Aliphatic Friedel Crafts Reactions" 21
Chapter 3: 1. Ojima and S.M. Brandstadter: "New Reactions of Ketene Silyl Acetals with Imines
Promoted by Titanium (IV) and Zirconium (IV) Chlorides" 37
Chapter 4: C. Gennari: "Stereoselective Synthesis with SHyl Ketene Acetals and TiCI4" 53
Chapter 5: G.E. Keck, S. Castellino and M.B. Andrus: "Mechanistic Variability in the Lewis Acid-
Promoted Reactions of Aldehydes with Organostannanes" 73
Chapter 6: M.T. Reetz: "Synthetic and Mechanistic Studies of Lewis Acid Mediated C-C-Bond
Formation" 107
Chapter 7: M. Santelli, A. Tubul and C. Morel-Fourrier: "Acylation of Alkenes and Allylsilanes" 127
Chapter 8: B.B. Snider: "Alkylaluminum Halide Induced Reactions of Carbonyl Compounds with
Unactivated Alkenes" 147
Chapter 9: G. Majetich, K. Hull, D. Lowery, C. Ringold and J. Defauw: "Intramolecular Additions
of Allylsilanes to Conjugated Dienones" 169
Chapter 10: H. Kunz: "Lewis Acid-Catalyzed Stereoselection on Carbohydrate Templates" 189
Chapter 11: H. Sakurai: "Lewis Acid Character and Selective Reactions of Pentacoordinate Silicon
Compounds" 203
Chapter 12: MJ. Taschner: "Synthesis of Clerodane Diterpenes Via Lewis Acid Catalyzed Cycload-
ditions" 227
Chapter 13: S.E. Denmark and T.M. Willson: "Studies on the Mechanism of Allylmetal-Acetal
Additions" 247
Chapter 14: 1. Fleming, D. Higgins and A.K. Sarkar: "Stereocontrol in Organic Synthesis Using
Silicon Compounds" 265
Chapter 15: H. Yamamoto, K. Maruoka and K. Furuta: "Chiral Lewis Acid Catalysts Or-
ganoaluminum and Boron Reagent" 281
viii
CONTRIBUTED POSTERS
C. Aubert, J.-P. Begue, D. Bonnet-Delpon and D. Mesureur: "Access to Trifluoromethyl Indans
by Cycloalkylation of ~ -Aryl Trifluoromethyl-Ketones" 295
C. Aubert, J.-P. Begue and D. Bonnet-Delpon: "A Route to Aliphatic Cycles Bearing a CF3
Group" 297
A.D. Brown, E.W. Colvin and M..J. Nugent: "Lewis Acid Promoted Synthesis of ~-Lactams" 299
H. Frauenrath: "Lewis Acid Promoted Rearrangements of Vinyl Actals -Basics and Applications" 301
H. Hagiwara, A. Okano, T. Akama and H. Uda: "Lewis Acid Promoted Sequential Multifold
Michael Reactions and Application to Syntheses of Terpenoids" 303
H. Hiemstra, L.L.M. Lolkema, H.H. Mooiweer and W.N. Speckamp: "Lewis Acid-Promoted
Cyclization Reactions by Way of Methoxycarbonyloxonium Ion Intermediates"
305
K. Krohn, W. Priyono, I. Hamann and J. Kohle: "Stereo-chemistry of Anthracyclinones: Chela-
tion Versus Non-chelation Control" 307
H. Mayr and G. Hagen: "Reactivity of Organosilicon Compounds towards Carbenium Ions" 309
I. Paterson: "Aldol Condensations of Ketones Using Chiral Boron Reagents" 311
O. Petrov and E. Winterfeldt: "Synthesis of Hydroazulenic Lactones" 313
T. Sato: "Lewis-Acid Induced Reactions of Organotin Compounds" 315
D. Schinzer, M. Kalesse and J. Kabbara: Silica Gel-Catalyzed Cyclizations of Mixed Ketene
Acetals" 317
M.F. Schlecht, H.-J. Kim and A. Guerrero: "Substituent-Directed Oxidation" 319
J. Seyden-Penne: "Lewis Acid Catalyzed Hetero Diels Alder Reactions" 321
D. Spilzner and P. Wagner: "Lewis Acid Catalized Double Michael Addition" 323
Subject Index ' 325
FOREWORD
The ASI workshop on "Selectivities in Lewis Acid Promoted Reactions" held in
the Emmantina-Hotel in Athens-Glyfada, Greece, October 2-7, 1988 was held
to bring some light into the darkness of Lewis acid induced processes.
As such the workshop reflects some current trends in organic synthesis, where
Lewis acids are becoming a powerful tool in many different modern reactions,
e.g. Diels-Alder reactions, Ene reactions, Sakurai reactions, and in general
silicon and tin chemistry.
The objective of this meeting was to bring together most of the world experts in
the field to discuss the major reactions promoted by Lewis acids.
Organic synthesis will play a major role in this book connected with some
fundamental mechanistic work on allylsilane and -tin chemistry. Both natural
product synthesis and unnatural molecules are presented in the chapters.
The book presents all the 15 invited lectures and the contributions of 15 posters.
I am confident that the material presented in this book will stimulate the
chemistry, which has been discussed on our meeting, around the world.
The meeting and the book were only possible through a grant of the NATO
Scientific Affairs Devision and financial support by the following companies:
Kali Chemie (Hannover, W-Germany), E. Merck (Darmstadt, W-Germany),
Sandoz (Basel, Switzerland), Schering (Berlin, W-Germany).
I grateful acknowledge the help of the Organizing Committee Dr. Jiirgen
Graefe and Prof. Horst KUllZ. In addition, many thanks are due to the graduate
students of my group in Hannover, especially to Dr. Christos Allagiannis, who
has done an excellent job in organizing most of the things on his home ground in
Athens to make this meeting a success.
Dieter Schinzer
ix
LIST OF PARTICIPANTS
Dr E. Akgun Dr N. Altintas
Research Institute for Basic Sciences Sezai Tlirkes Feyzi Akkaya
Chemistry Department Holding CO.
P.O.Box 74 81190 Altunizade-Camlica
41401 Gebze-Kocaeli Istanbul
Turkey Turkey
Dr Ekkehard Baader Prof. B.M. Baysal
HOECHTS AG, Pharma Synthese G 838 Technical University of Istanbul
Postfach 80 03 20 Faculty of Sciences
D-6230 Frankfurt/Main 80 Department of Chemistry
F.R.G. Maslak-Istanbul
Turkey
Dr J.-P. Begue Prof. D. Bonnet-Delphon
CNRS-CERCOA CNRS-CERCOA
Rue Henri Dunant Rue Henri Dunant
94320 Thiais 94320 Thiais
France France
Dr Henning Bottcher Dr Rolf Bohlmann
E. Merck Pha Fo Chern. HK Schering AG
Frankfurter Str. 250 Institut fur Arzneimittelchemie
D-6100 Darmstadt D-1000 Berlin 65
F.R.G. F.R.G.
Matthias Bratz Dr E.W. Colvin
Institut fur Organische Chemie Chemistry Department
Universitat Gottingen University of Glasgow
Tammanstr. 2 Glasgow G12 8QQ
D-3400 Gottingen U.K.
F.R.G.
Dr A.P. Davis Prof. A.S. Demir
Department of Chemistry Department of Chemistry
Trinity College Middle East Technical University
Dublin 2 06531 Ankara
Ireland Turkey
xi
xii
Scott G. Dernnark Dr I. Fleming
Department of Chemistry University Chemical Laboratory
University of Illinois Lensfield Road
Illinois Cambridge CB2 lEW
U.S.A. U.K.
Dr H. Frauenrath Cessare Gennari
Institut fur Organische Chemie Dipartimenti di Chimica Organica
TH Aachen Universita di Milano
D-5100 Aachen Milano
F.R.G. Italy
Dr J. Graefe Dr D. Grotjahn
Schering AG c/o Prof. Dotz
Postfach 1540 FB Chemie der Universitat Marburg
4701 Bergkamen D-355 Marburg 1
F.R.G. F.R.G.
Dr J. Hackenbruch Prof. H. Hagiwara
HOECHST AG Chemical Research Institute of
Werk Griesheim Non-aqueous Solutions
Postfach 83 12 51 Tohoku University, Katahira
D-6230 Frankfurt 83 Sendai 980
F.R.G. Japan
Dr Michael Harre Prof. Dr G. Helmchen
Schering AG Organisch~Chemisches Institut
Pharma Syntheseoptimierung der Universitat
Postfach 65 03 11 1m Neuenheimer Feld 270
D-l000 Berlin 65 D-6900 Heidelberg 1
F.R.G. F.R.G.
Dr H. Hiemstra Dr C.B. Hilton
Laboratory of Organic Chemistry HOECHST Celanese
University of Amsterdam 1901 Oakwood Road
Nieuwe Achtergracht 129 P.O. Box 9077
1018 WS Amsterdam Corpus Christi, Texas 78469-9077
The Netherlands U.S.A.
Prof. H.M.R. Hoffmann Dr D.E. Kaufmann
Institut fur Organische Chemie Bayer AG / Q 18/3
Universitat Hannover D-509 Leverkusen/Bayerwerk
Schneiderberg lB F .R.G.
3000 Hannover 1
F.R.G.