Organic Synthesis Highlights IV

371 Pages·2000·7.17 MB·English

Organic Synthesis Highlights IV
Edited by Hans-Giinther Schmalz
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Organic Synthesis
Highlights IV
Edited by
Hans-Gunther Schmalz
@WILEYVCH
Weinheim . New York . Chichester . Brisbane . Singapore . Toronto
Prof. Dr. Hans-Gunther Schmalz
Institut fur Organische Chemie
dcr Universitat zu Koln
Greinstrasse 4
D-50939 Koln
Germany
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Preface
During the past century, the world has changed to and enantioselective catalysis. The second part
an unprecedented extent, and the development of focuses on applications in total synthesis of nat-
the chemical sciences has greatly contributed to ural products and non-natural compounds and
this change. The ability of chemists to synthesize materials. In addition, a few articles reflect the
complex organic molecules such as dyes, drugs, recent renaissance of solid-phase synthesis and
fragrances and crop protection agents is largely the growing importance of combinatorial che-
responsible for the high standard of living we mi stry.
enjoy today. Moreover, synthesis as a key dis- The articles taken from “Synthese im Blick-
cipline is contributing to the development of punkt” have all been carefully updated and trans-
modern life sciences and materials technology. lated by the authors (U. Koert, 0. Reiser, M.
However, while the power of synthesis has led Reggelin, C. Ruck-Braun). I would like to ex-
to remarkable achievements, the technology press special thanks to these colleagues and their
and art of organic synthesis is still far from being co-workers. I am also grateful to all the other
fully developed. Many problems remain unsolved authors for their excellent and up-to-date contri-
concerning, for instance, the efficiency and butions. I also have to thank the team at Wiley-
atom-economy of syntheses. Organic synthesis VCH, especially Dr. A. Eckerle, Dr. G. Walter,
continues to offer multifarious academic and Dr. A. Kessinger and P. Biel for their excellent,
technological challenges, and a tremendous professional support and their patience with the
amount of research is carried out worlwide in editor.
this field. I hope this new volume will find as much
This fourth volume of Organic Synthesis High- acceptance in the scientific community as the
lights (OSH) comprises a collection of more first three volumes of this series and will help
than 40 articles reflecting some more recent de- to stimulate the interest of, in particular, young
velopments and achievements of organic synth- chemists in the field of synthesis.
esis. About half of the contributions have their
origin in the review section “Synthese im Blick- Cologne, February 2000
punkt” in Nachrichten aus Chemie, Technik Hans-Giinther Schmalz
und Labnratorium (1994- 1998), the members’
journal of the GDCh; most of the others have
been selected from the “Highlights” of An-
gewandte Chemie (1997- 1998). The first half
of the present volume concerns synthetic metho-
dology, with emphasis on stereoselective synth-
esis, transition metal organometallic methods,
Contents
Part I. Synthetic Methods
A. New Methods in Stereoselective Synthesis
Stereocontrolled Simmons-Smith Cyclopropanation .............................. 3
Julia Schuppan and Ulrich Koert
Oppolzer Sultams ...................................................... 11
Oliver Reiser
Oxazolines: Chiral Building blocks, Auxiliaries and Ligands ........................ 17
Martin Glos and Oliver Reiser
New Sequential Reactions with Single Electron Transferring Agents ................... 34
Troels Skrydstrup
Deracemisation by Enantiodifferentiating Inversion in 1,3- and I ,2-Diols ............... 40
Anthony I? Davis
Non-Biaryl Atropisomers: New Classes of Chiral Reagents, Auxiliaries and Ligands? ...... 48
Jonathan Clayden
Amino Acid Derivatives by Multicomponent Reactions ............................ 53
Gerald Dyker
New Polyol Syntheses ................................................... 58
Christoph Schneider
Stereoselection at the Steady State: The Design of New Asymmetric Reactions ........... 67
Thomas Wirth,
B. Transition Metal Organometallic Methods
Photolysis of Fischer Carbene Complexes ..................................... 7 1
Oliver Kiehl and Hans-Gunther Schmalz
Zr-Catalyzed Carbomagnesation of Alkenes .................................... 77
Florian Blume and Hans-Gunther Schmalz
VIII Contents
Intramolecular Alkoxypalladation .......................................... 83
Oliver Geis and Hans-Giinther Schmalz
Ring-closing Olefin Metathesis ............................................ 91
Michael Kurle and Ulrich Koert
Metal-Catalyzed Hydroformylations ........................................ 97
Oliver Reiser
Rare Earth Metal Catalysts .............................................. 104
Patrick Amrhein and Kurola Ruck-Bruun
Dithioacetals as an Entry to Titanium-Alkylidene Chemistry:
New and Efficient Carbonyl Olefination ..................................... 110
Bernhurd Breit
New Developments in the Pauson-Khand Reaction .............................. 116
Oliver Geis and Huns-Giinther Schmalz
Multicomponent Catalysis for Reductive Bond Formations ........................ 123
Alois Fiirstner
Natural Product Synthesis by Rh-mediated Intramolecular C-H Insertion .............. 130
Douglass I? Taber and Suluh-E. Stiriba
C. Enantioselective Catalysis
Enantioselective Heck Reactions ........................................... 136
Marku.5 Jachmann and Hans-Giinther Schmalz
Catalytic Asymmetric Aldol Reactions ...................................... 144
Rolf Krauss and Ulrich Koert
Binaphthyls: Universal Ligands for Catalysis .................................. I55
Tobias Wubnitz and Oliver Reiser
Fluorotitanium Compounds - Novel Catalysts for the Addition of Nucleophiles
to Aldehydes ........................................................ 166
Rudolf 0. Duthaler and Andreas Hufner
Enzymes and Transition Metal Complexes in Tandem - a New Concept for Dynamic
Kinetic Resolution .................................................... 172
Ruiner Stiirmer
Non-Enzymatic Kinetic Resolution of Secondary Alcohols ........................ 175
Peter Somfai
Copper-Catalyzed Enantioselective Michael Additions: Recent Progress with New
Phosphorus Ligands ................................................... 182
Norbert Krause
C,-Symmetric Ligands for Catalysis ........................................ 187
Mark Mikula's and Kurola Ruck-Bruun
Highly Enantioselective Catalytic Reduction of Ketones Paying Particular Attention to
Aliphatic Derivatives ................................................... 194
Renat Kadyrov and Riidiger Selke
Contarits IX
Part 11. Applications
A. Total Synthesis of Natural Products
Total Synthesis of Ikarugamycin ........................................... 207
Oliver Schwarz and Hans-Gunther Schmulz
Palladium-Catalyzed Synthesis of Vitamin D-Active Compounds .................... 2 I2
Sandra Kruuse and Huns-Gunther Schmnlz
Syntheses of Oligo(thiazo1ine) Natural Products ................................ 2 18
Subine Hoppen and Ulrich Koert
Camptothecin - Synthesis of an Antitumor Agent ............................... 232
Stcfun Biiurle and Ulrich Koert
Polycyclic Guanidines From Nature's Shaped Cations to Abiotic Anion Hosts ........... 241
Hans-Dieter Arndt und Ulrich Koert
Synthetic Access to Epothilones - Natural Products with Extraordinary Anticancer Activity . 25 I
Ludger A. Wessjohunn und Giinther Scheid
Total Syntheses of the Marine Natural Product Eleutherobin ....................... 268
Thonius Lindel
Selectin Inhibitors ..................................................... 275
Murkiis Riisch und Kurola Riick-Bruun
Crossing the Finishing Line: Totdl Syntheses of the Vancomycin Aglycon .............. 281
Holger Herzner and Kurola Riick-Braun
B. Synthesis of Non-Natural Compounds and Materials
An Update on the New Inductees in the ,,Hall of Phane" - No Phane, No Gain! ......... 289
Graham -1. Bodwell
Well-Rounded Research: Nanotubes through Self-Assembly ........................ 30 1
Burkhurd Kiinig
From Random Coil to Extended Nanocylinder: Dendrimer Fragments Shape Polymer Chains 306
Holger Frey
C. Solid Phase Synthesis and Combinatorial Chemistry
Combinatorial Methods - Prospects for Catalysis? .............................. 3 I4
Reinhard Racker and Oliver Reiser
The Renaissance of Soluble Polymers ....................................... 322
M. Reggelin
Polymeric Catalysts .................................................... 328
M. Reggelin
Combinatorial Chemistry for the Synthesis of CarbohydrateKarbohydrate Mimics Libraries . 337
Prubhat Arya, Robert N. Ben and Kristina M. K. Kutterer
Combinatorial Biosynthesis of Polyketides .................................... 343
Kui Donsbuch and Kamla Ruck-Braun
Index .............................................................. 351
List of Contributors
Dr. P. Arya Prof. Dr. G. Dyker
Steacie Inst. f. Mol. Sciences FB6-Inst. f. Synthesechemie
Nat. Research Council of Canada der Universitat-GH Duisburg
100 Sussex Drive Lotharstr. I
CanadaKlA OR6 Ottawa 47048 Duisburg
Dr. G. J. Bodwell Dr. H. Frey
Department of Chemistry Inst. fur Makromolek. Chemie
Memorial University of NF (FMF), Universitat Freiburg
KanadaAlB 3x7 St. John’s Stefan-Meier Str. 21/31
Priv.-Doz. Dr. B. Breit Prof. Dr. A. Fiirstner
Organisch-Chemisches Institut Max-Planck-Institut
der Universitat Heidelberg fur Kohlenforschung
Im Neuenheimer Feld 270 Kaiser-Wilhelm-Platz I
69120 Heidelberg 45470 Miilheim
Dr. J. P. Clayden Prof. Dr. N. Krause
Department of Chemistry Lehrst. fur Organische Chemie
University of Manchester Universitat Dortmund
Oxford Rd. 44221 Dortmund
M13 9PL Manchester
Prof. Dr. U. Koert
Institut fur Chemie
Prof. A. P. Davis
Department of Chemistry der Humboldt-Universitat
(University of Dublin Hessische Str. 1-2
Trinity College 10115 Berlin
Ir-2 Dublin
Prof. Dr. B. Konig
Dr. R. Duthaler Inst. fur Organische Chemie
Novartis Pharma AG der Universitat Regensburg
WSJ-507.109 Universitatsstr. 3 1
Postfach 93053 Regensburg
4002 Base1
XI1 List of Contributors
Dr. T. Lindel Prof. Dr. T. Skrydstrup
Pharmazeut.-chem. Institut Department of Chemistry
der Universitat Heidelberg University of Aarhus
Im Neuenheimer Feld 364 Langelandsgade I40
69 120 Heidelberg DK-8000 AarhudDenmark
Dr. M. Reggelin Prof. Dr. R. Selke
Institut fur Organische Chemie Ifok, ,,Asymmetrische Katalyse"
Universitat Mainz an der Universitat Rostock
Dusbergweg 10- 14 Buchbinderstr. 5-6
55099 Mainz 18055 Rostock
Prof. Dr. 0. Reiser Dr. P. Somfai
Institut fur Organische Chemie Dept. of Organic Chemistry
der Universitat Regensburg Stockholm University
Universitatsstr. 3 1 Arrhenius Laboratory
93053 Regensburg 10691 StockholmE
Dr. R. Sturmer BASF AG
Dr. K. Ruck-Braun Hauptlaborat., ZHF/D A30
Institut f. Organische Chemie 67056 Ludwigshafen
J. Gutenberg-Universitat Mainz
Duesbergweg 10- 14 Prof, Dr. D. F. Taber
55099 Mainz Dept. of Chemistry
and Biochemistry
Prof. Dr. H.-G. Schmalz University of Delaware
Inst. fur Organische Chemie USA 197 16 Newark
Universitat Koln
GreinstraRe 4 Prof. Dr. L. A. Wessjohann
50939 Koln Faculty of Chemistry (N 348)
Vrije Universiteit Amsterdam
Dr. C. Schneider de Boelelaan 1083
Institut fur Organische Chemie HV 1081 Amsterdam
der Universitat
Tammannstr. 2 PD Dr. T. Wirth
37077 Gottingen Institut fur Organische Chemie
Universitat Basel
St. Johanns-Ring 19
4056 Basel