Table Of Content

T. Kinzel, F. Major, C. Raith, T. Redert, G?WllEY-VCH F. Stecker, N. Tólle, J. Zinngrebe Organic Synthesis Workbook 111 Foreword by Matthias Beller Tom Kinzel, Felix Major, Thomas Redert, FIarían 5tecker, Julia Zinngrebe, Nina Talle, and Christian Raith Organic Synthesis Workbook 111 1807-2007 Knowledge for Generations Each generation has its unique needs and aspirations. When Charles Wiley first opened his small printing shop in lower Manhattan in 1807, it was a generation of boundless potential searching for an identity. And we were there, helping to defme a new American literary tradition. Over half a century later, in the midst of the Second Industrial Revolution, it was a generation focused on building the future. Once again, we were there, supplying the critical scientific, technical, and engineering knowledge that helped frame the world. Throughout the 20th Century, and into the new millennium, nations began to reach out beyond their own borders and a new international community was born. Wiley was there, expanding its operations around the world to enable a global exchange of ideas, opinions, and know-how. For 200 years, Wiley has been an integral part of each generation s journey, en abling the flow of information and understanding necessary to meet their needs and fulfill their aspirations. Today, bold new technologies are changing the way we live and learn. Wiley will be there, providing you the must-have knowledge you need to imagine new worlds, new possibilities, and new opportunities. Generations come and go, but you can always count on Wiley to provide you the knowledge you need, when and where you need it! a--~~ William J. Pesce Peter Booth Wiley President and Chief Executive Officer Chairman of the Board Tom Kinzel, Felix Major, Thomas Redert, Florian Stecker, Julia Zinngrebe, Nina Talle, and Christian Raith Organic Synthesis Workbook 111 BICENTENNIAL i.J 1 8 o 7 •~ z z ~ @WILEY ~ z z ~ 2007 ~ - > • r WI LEY-VCH Verlag GmbH & Co. KGaA The Authors All books published by Wiley-VCH are care ful1y produced. Nevertheless, authors, editors, Tom Kinzel, Felix Major, Thomas Redert, and publisher do not warrant the information F/orian Stecker, Julia Zinngrebe, Nina Tlille, contained in these books, including this Christian Raith book, to be free of errors. Readers are advised U niversity of Giittingen to keep in mind that statements, data, illus Institute for Organic and Biomolecular trations, procedural detalls or other items Chemistry may inadvertently be inaccurate. Tammannstr. 2 37077 Giittingen Library of Congress Card No.: Applied for Germany British Library Cataloguing-in-Publication Data: A catalogue record for this book is available from the British Library. Bibliographic information published by the Deutsche Nationalbibliothek Die Deutsche Na tionalbibliothek lists this publication in the Deutsche Nationalbiblio grafie; detailed bibliographic data are avail able in the Internet at <http://dnb.d-nb.de>. © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim All rights reserved (including those of trans lation into other languages). No part of this book may be reproduced in any form - by photoprinting, microfilm, or any other means - nor transmitted or translated into a machine language without written permis sion from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Printing Strauss GmbH, Miirlenbach Bookbinding Litges & Dopf GmbH, Heppenheim Cover Anne Christine Kegler, Grafik-Designerin, Karlsruhe Wiley Bicentennial Logo Richard J. Paófico Printed in the Federal Republic of Germany. Printed on aód-free papero ISBN: 978-3-527-31665-6 The Authors Tom IGnzel, born in 1977 in Erfurt, Germany, started studying chemistry at the University of Giittingen, Ger many, in October 1998. After staying in the Peoples Repub lic of China in 2001/2002 studying Chinese at the Univer sity ofNanjing and joining the working group ofProfessor Wolfgang Hennig at the Chinese Academy of Sciences in Shanghai, he returned to Giittingen and received his diplo ma in Chemistry in July 2004. He is now a doctoral re searcher in the research group of Professor Lutz F. Tietze and employs experimental and theoretical techniques for mechanistic studies and method development in the field of stereoselective homoallylic ether synthesis. Dr. Felix Major, born in 1977 in Wittmund, Germany, started studying chemistry at the University of Giittin gen, Germany, in October 1998. After joining the group of Professor Jonathan Clayden at the University of Manchester for three months in 2002 he returned to Giittingen and accomplished his diploma in Septem ber 2003 under the guidance ofProfessor Lutz F. Tietze. In November 2006, he gained his doctorate in the same research group with a thesis on the synthesis and biolo gical evaluation of prodrug analogues of the antibiotic CC-1065 for a selective treatment of cancer. Christian Raith was born in 1980 in Giittingen, Ger many, and started studying chemistry at the University of Giittingen, Germany, in October 2001. He joined the research group of Professor Lutz F. Tietze in May 2005 and received his diploma in January 2006. He is now doing his doctoral research in the same group studying palladium-catalyzed enantioselective domino reactions for the synthesis of chromanes. Organic Synthesis Workbook 1J I. Tom Kinzel. Felix Major, Thomas Redert, Florian Stecker, Julia Zinngrebe, Nina Tolle. Christian Raith Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-31665-6 Thomas Redert, bom in 1978 in Gieí?en, Germany, started studying chemistry at the University of Gottin gen, Germany, in October 1999. After staying in the United Kingdom in 2002/2003 at the University ofNew castle upon Tyne and joining the working group of Dr. Julian G. Knight, he retumed to Gottingen and received his diploma in chemistry in July 2004. He is currently a doctoral researcher at the University of Gottingen in the research group of Prof. Lutz F. Tietze. His research deals with the application of Palladium-catalyzed domi nocyclizations for the synthesis of natural product ana logues. FIorían Stecker, bom in 1980 in Eutin, Germany, re ceived his diploma in organic chemistry from the Uni versity of Gottingen, Germany, in July 2004. He started studying chemistry in Gottingen in October 1999 and worked at the Université Pierre et Marie Curie, Paris VI, France, under the direction of Professor Max MaIa cria in 2002/2003. Shortly thereafter, he joined the group of Professor Lutz F. Tietze in Gottingen, where he is currently a doctoral researcher. He is committed to the palladium catalyzed domino-Wacker-Heck reac tion for the enantioselective synthesis of vitamin E and other closely related chromanes and chromenes. Nina Tolle, bom in 1981 in Osnabrück, Germany, started studying chemistry at the University of Gottin gen, Germany, in 2001. She joined the research group of Professor Tietze in 2005 and received her diploma in 2006. She stayed in the same group for her doctoral research which deals with Lewis-acid mediated domino reactions for the synthesis of spiroamine structures with the objective of natural product synthesis. Dr. Julia Zinngrebe, bom in 1979 in Eschwege, Ger many, started studying chemistry at the University of Gottingen, Germany, in October 1998. After joining the group of Professor Clayden at the University of Manchester for three months in 2002 she returned to Gottingen and accomplished her diploma in September 2003 under the guidance of Professor Tietze. In January 2007, she gained her doctorate in the same research group with a thesis on Palladium-catalyzed domino-re actions for the enantioselective synthesis of Vitamin E. Dedicated to our PhD supervisor Pro! Dr. Dr. h. c. L. F. Tietze on the occasion ofhis 65th birthday Foreword Organic synthesis is at the heart of chemistry. Although today interdisciplinary areas between chemistry and biology or between chemistry and material sciences are ofien believed to provide the main driving forces for the advancement of chemistry, I am convinced that the development of efficient and environmentally benign synthetic methods is still one of the most important goals of current chemical research. Significantly, a majority of all chemists doing research in industry or academia are faced in their daily lives with demands for the efficient synthesis of new molecules. It is thus important to attract the interest of talented students for this area and to provide high quality education. From the beginning, the Organic Synthesis Workbook has been devoted to a significant extent to the training and education of students and younger researchers in this direction. The main concept is to present challenging synthetic problems to the reader, which are selected from state-of-the-art syntheses of natural products. The present 3rd volume successfully follows this track. The new Organic Synthesis Workbook - similar to its predecessors - has been carefully devised and realized by a group of creative young students from the Institute of Organic and Bio molecular Chemistry ofthe Georg-August-University ofGottingen, Germany.1t covers 14 well selected synthetic problems including modern catalytic coupling reactions and metathesis chemistry, together with recent developments in stereoselective carbon-carbon and carbon oxygen bond formation. More specifically, each problem is introduced to the reader in a general marmer. Afier this introduction the key chemistry of the respective synthesis is explained. Then, the various synthetic problems are presented in a clear and understandable manner. The major difference to classical teaching books is the active interaction ofthe reader with the content. One could ask, is the concept ofthis book still timely? In my opinion, definitely yes! Obviously, information pours out from all kinds of scientific journals, PowerPoint presentations, and especially the internet. However, to acquire long-Iasting knowledge of organic synthesis, and to transfer this knowledge, it is essential not only to consume facts and data but to apply it to real synthetic problems. Thus, in addition to students for Masters and PhD degrees, everyone interested in synthetic chemistry is encouraged to train actively with books such as this. Finally, 1 wish to congratulate the authors for their excellent achievement. It remains for me to hope that readers will enjoy working with this volume and discover aspects that will stimulate their own future research. Matthias Beller Rostock, 20.11.2006