Tom Kinz, Felie Major Thomas Rede, Flvian Stecker, Julia Zinngrebe, Nina Tal, ‘and Christian Roth ‘Organic Syrthesis Workbook I11807-2007 Knowledge for Generations Bach generation has its unigue needs and aspirations. When Chatles Wily first ‘opened his small printing shop in lower Manhattan in 1807, i was a generation ‘of boundless potential searching for an identity. And we were there, helping to define 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 fiame the world. Throughout the 20% Century, and into the new millennium, natiors began to reach out beyond their own borders and a new international community was bora. Wiley was there, expanding its operations around the word to enable global exchange of ‘eas, opinions, and know-how For 200 years, Wiley has been an integral part f each generation s journey, en- bling the flow of information and understanding necessary to meet their needs sind fulfil their aspirations. Today, bold new technologies are changing the way We live and leam. Wiley wil be there, providing you the musthave knowledge you need to imagine new worlds, new possibilities, and new opportunities ‘Generations come and go but you can always enunt on Wiley to provide you the knowledge you need, when and where you need it Uteinnf Pasee_ TE Eile, 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 Tolle, and Christian Roith Organic Synthesis Workbook II 1807 |@WILEY| 2007 WILEY-VCH Verlag GmbH & Co. KGaATo tna, al Mj, haa abr, Flnan Secs ote Zn, Nn Tal, ater of ange ‘A ons pad y Wey VCH case {ay tnd Newtson lor {lbs dor waa an tebe of eed te eed toe in mind sen a Lis fangs at No: Apel sh ba CtosngPbenon Dut: ‘Naar ond fre ck sae fone tt tary epic ineation ped ye i ead taste ae i fe deed Whip da ak ‘Sein hc tee hp es ‘Al gis sere cig Hae ws Tan ie te ngage yar of ‘eck maybe prada nay f= by Poeiine malin. oe ens Son forte pers Regier! nan doa edi ek en soapy are mach art ene npc he Png Sas Gab Make olny Lies & op Cb 7 (ree Chitin ee, tfl-Devgnrn Kate ‘Wey Scene Lng FenThe Authors Cap WILEY VCH Vg Gal Ce LA Meee” Stan Bah ‘Tom Kinzel, born in 1977 in Esfart, Germany, stated studying chemistry at the University of Gatingen, Get ‘many in October 1988, After stayingin the Peoples Repub lic of China in 2001/2002 studying Chinese a the Univer sity of Nanjing an joining the working group of Profesor Wolfgang Hennig at the Chinese Academy of Sciences in Shanghai, he returned to Gitingen and received his dip ‘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 thearetical techniques for ‘mechanistic studies and method development in the Geldof stereoselective homeallylic ther synthesis, De. Felix Major, born in 1977 in Wittmund, Germany, started studying chemistry atthe University of Gettin gen, Germany, in October 1998. ARer joining the group of Professor Jonathan Clayden atthe Univesity ‘of Manchester for three months in 2002 he returned to Gottingen and accomplished his diploma in Septem: ber 2003 under the guidance of Prafesor Lit F. Tietze In November 2006, he gained his doctorate in the same research group with a thesis on the synthesis and biol gical evaluation of prodrug analogues of the antibiotic ‘CC-1065 for a selective treatment of cancer. (Christian Raith was bom in 198) in Gottingen, Gee many and started studying chemistry atthe University of Gottingen, Germany, in October 2001. He joined the reseatch group of Professor lute 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 chramanes‘Thomas Redert, born in 1978 in Gieen, Germany, started studying chemisty atthe University of Géttin gen, Germany, in Octber 1999. After staying in the United Kingdom in 2002/2003 atthe University of New: castle upon Tyne and jcining the working group of Dr. Julian G. Knight, he etumed to Géttingen and received his diploma in chemistry in July 2008 He is currently a doctoral researcher atthe University of Gétingen inthe research group of Prof. Lutz F. Tietze. His research deals withthe application of Plladium-atalyzed domi- nocyclizations for the synthesis of natural product ana logue. Florian Stecker, born 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 Universit Pierre et Marie Cue, Paris VI, France, under the direction of Professor Max Mal cia in 2002/2003, Shortly thereafter, he joined the group of Professor Lutz F. Tietze in Géttingen, where he is curently a doctoral researcher. He is committed to the palladium catalyed domino: Wacker Heck rea tion for the enantoseective synthesis of vitamin E and other closely related chromanes and chromenes. Nina Tolle, born in 1981 in Osnabrick, Germany, started studying chemistry at the University of Gettin gen, Germany, in 2001. She joined the research group of Professor Tietze in 2005 and received her diploma fn 2006, She stayed in the sime group tor her doctoral research which des wih Levieacid mediated domino reactions for the synthesis of spiroamine structures wit the objective of natural product synthesis. Dr, Julia Zinngrebe, bam in 1979 in Eschwege, Gee ‘many, stated studying chemistry at the University of Gottingen, Germany, ia October 1998. After joining the group of Professor Clayden at the University of Manchester for three months in 2002 she retired to GGattingen and accomplished her diploma in September 2003 under the guidance of Professor Tietze. In January 2007, she gained her doctorate in the same research troup with a thesis on Palladiun-atalyzed domino xe- actions fr the enantioselective synthesis of Vitamin EDedicated 10 our PhD supervisor Prof. Dr. Dr. h.c. L. F. Tietze ‘on the occasion of his 65th birthdayForeword Organic synthesis is atthe heart of chemisty. Although today interdsciplinary areas between chemistry and biology or between chemistry and material scences ae often believed to provide the main driving fore for the advancement of chemistry, Iam convinced that the development of efficient and environmentally benign synthetic methods i tl 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 significant extent tothe training and education of students and younger researchers inthis direction. The main concept isto present challenging synthetic problems to the reader, ‘which are selected from state-of-the-art syntheses of natural products. The present 3° volume successfully follows this track. ‘The new Organic Synthesis Workbook - similar to its predecessors ~ has been carefully devised and realized by & group of creative young students from the Institute of Organic and Bio- ‘molecular Chemistry of the Geong-August-University of G@tingen, Germany. It covers 14 well- selected synthetic problems including modem 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 ‘manner. After this introduction the key chemistry ofthe 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 withthe content, (One could as, isthe concept ofthis book sil timely? In my opinion, definitely yes! Obviously, information pours out from all kinds of scientific jourls, PowerPoint presentations, and especially the internet. However, to acquire long-lastisig knowledge of organic synthesis, and to transfer this knowledge, itis essential not only to consume fats 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 a this Finally I wish to congratulate the authors for their excellent achievement. It remains for me 10 hope that readers will enjoy working with this volume and discover aspects that will stimulate theie own future research (Que Mathias Beller Rostock, 20.11.2006