MODERN SYNTHETIC METHODS
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1 MODERN SYNTHETIC METHODS Volume Editor: Prof. Dr. Rolf Scheffold Institut fur organische Chemie der Un ivers it at Bern FreiestraBe 3 CH-3012 Bern
2 MODERN SYNTHETIC METHODS Editor: R. Scheffold Volume M. Makosza, Naked Anions-Phase Transfer A. Patchornik, Polymer Supported Reagents D. Seebach, S- and Se-Reagents 1976 Verlag Sauerlander, Otto Salle, Aarau und Frankfurt am Main Volume L. Eberson, Electro-Organic Synthesis Chiral Building Blocks in Enantiomer Synthesis: D. Seebach - ex Tartaric Acid A. Vasella - ex Sugars A. Fischli - Using Enzymatic Transformations 1980 Verlag Sauerlander, Otto Salle, Aarau und Frankfurt am Main Volume Transition Metals in Organic Synthesis: J. K. Stille, Principles and Rules L. S. Hegedus, Group VIII Transition Metals J.F. Normant, Copper and Manganese D. Seebach, Titanium and Zirconium R. Scheffold, B12 and Related Cobalt Complexes 1983 Verlag Sauerlander, Otto Salle, Aarau und Frankfurt am Main Coedition by John Wiley & Sons, Inc., Chichester
3 MODERN SYNTHETIC METHODS 1986 SOUND AND LIGHT IN SYNTHESIS K. S. Suslick, Ultrasound in Synthesis K. Schaffner, Photochemically Generated Building Blocks M. Demuth, Natural Product Synthesis by Photochemical Methods SYNTHESIS OF ENANTIOMERICALL Y PURE COMPOUNDS WITH C,C BOND FORMATION D. Seebach -via Acetals and Enamines G. Helmchen -by Asymmetric Diels-Alder Reactions H. C. Brown -via Chiral Organoboranes Conference Papers of the International Seminar on Modern Synthetic Methods 1986 Interlaken, April 17thl18th 1986 Chairman: R. Scheffold Sponsored and Organized by The Association of Swiss Chemists Springer-Verlag Berlin Heidelberg New York Tokyo
4 Prof. Dr. Rolf Scheffold Institut fur organische Chemie der Universitat Bern, FreiestraBe 3 CH-3012 Bern Copyright Cover Design by Verlag Sauerlander, Aarau/Schweiz ISBN-13: e-isbn-13: : / Library of Congress Cataloging-in-Publication Data. International Seminar on Modern Synthetic Methods 1986 (1986 : Interlaken, Switzerland) Sound and light in synthesis. (Modern synthetic methods ; v. 4) 1. Chemistry, Organic-Synthesis-Congresses. 2. Ultrasonics Congresses. 3. Photochemistry-Congresses. 1. Scheffold, Rolf. II. Schweizerischer Chemiker Verband. III. Title. IV. Series. QD262.I ' This work is subject to copyright. All rights are reserved, whether the whole or part ofthe material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machine or similar means, and storage in data banks. Under 54 ofthe German Copyright Law where copies are made for other than private use, a fee is payable to "Verwertungsgesellschaft Wort", Munich. by Springer-Verlag Berlin Heidelberg 1986 Softcover reprint of the hardcover 1 st edition 1986 The use of registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher cannot assume any legal responsibility for given data, especially as far as directions for the use and the handling of chemicals are concerned. This information can be obtained from the instructions on safe laboratory practice and from the manufacturers of chemicals and laboratory equipment. 2152/
5 Dedicated to Vladimir Prelog Nobel Laureate
6 Pre f ace This paperback is the conference documentat10n of the forth Seminar on MODERN SYNTHETIC METHODS. It is the aim of these triennial Interlaken Sem1nars to provide a proper, concise and "ready for use" access to 1mportant and rapidly developing areas of synthet1c organ1c chem1stry. The two main themes of the 1986-Seminar are "Sound and Light in Synthesis" and "Synthesis of Enantiomerically Pure Compounds by C,C Bond Format10n". The first topic concerns the application of ultrasound in synthesis as well as the photochemical generation of build1ng blocks and their transformations into natural products. The second topic reflects the enormous progress in experience and understanding of organic chemistry directed towards the synthesis of enantiomerically pure compounds. This paperback is the compilation of the contributions prov1ded by the six lecturers, each a leading expert in his f1eld. The rev1ews are praxisoriented, they descr1be the basic concepts, the1r application 1n organic synthes1s and conta1n as an integral part representative exper1mental procedures. It 1S hoped that th1s book will serve as a gu1de for chem1sts interested in the art of modern organic synthes1s. Bern, 31. Januar 1986 Ro If Scheffo 1 d
7 Contents SOUND AND LIGHT IN SYNTHESIS Ultrasound in Synthesis.... Kenneth S. Suslick School of Chemical Sciences, University of Illinois at Urbana-Champaign 505 S. Mathews Av. Urbana, Illinois 61801, U. S. A. Photochemically Generated Building Blocks I The Tricyclooctanone Approach to Polyquinane Synthesis (Part I) The Underlying Photochemistry Kurt Schaffner and Martin Demuth Max-Planck-Institut fur Strahlenchemie Stiftstrasse 34-36, D-4330 Mulheim a. d. Ruhr Photochemically Generated Building Blocks II The Tricyclooctanone Approach (Part II). Photochemical Methods in Cyclopentanoid Natural Products Synthesis - A Comparison Martin Demuth Max-Planck-Institut fur Strahlenchemie Stiftstrasse 34-36, D-4330 Mulheim a. d. Ruhr SYNTHESIS OF ENANTIOMERICALL Y PURE COMPUNDS WITH C,C BOND FORMATION EPC Syntheses with C, C Bond Formation via Acetals and Enamines Dieter Seebach, Rene 1mwinkelried and Theodor Weber Laboratorium fur Organische Chemie der ETH-Zurich, Universitatsstrasse 16, CH-8092 Zurich. Asymmetric Diels-Alder Reactions with Chiral Enoates as Dienophiles 261 Gunter Helmchen, R. Karge and J. Weetman Organisch-Chemisches 1nstitut der Universitat Heidelberg, 1m Neuenheimer Feld 270. D-6900 Heidelberg. Enantiomerically Pure Compounds via Chiral Organoboranes Herbert C. Brown, Prabhakar K. Jadhav and Bakthan Singram Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, U. S. A.
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