Stereoselective Synthesis of Drugs and Natural Products, 2 Volume Set

Vasyl Andrushko is Research Scientist at Karlsruhe Institute of Technology where he researches in the areas of organic synthetic chemistry, asymmetric catalysis with application in stereoselective drug synthesis and as well as catalysis in alternative reaction media, organometallic chemistry, supramolecular and cluster chemistry. He has published 16 papers on topics directly related to stereoselective drug synthesis. Natalia Andrushko is a scientist at the Leibniz-Institute for Catalysis at the University of Rostock where she researches in the areas of organic and bioorganic chemistry, stereoselective synthesis of drugs and asymmetric catalysis. She has published 16 papers on topics directly related to stereoselective drug synthesis.

• PrefaceList of contributorsList of symbols and abbreviationsPART 1: GENERAL METHODS AND STRATEGIESChapter 1: Principles, concepts and strategies of stereoselective synthesisVasyl Andrushko and Natalia AndrushkoChapter 2: Chiral auxiliaries in drug synthesisStanley Chang, Shira D. Halperin, Jarod Moore and Robert BrittonChapter 3: Solid-phase organic synthesis of drugs and natural productsPeter J. H. ScottChapter 4: Asymmetric phase-transfer catalysisKohsuke Ohmatsu, Daisuke Uraguchi, and Takashi OoiChapter 5: Microwave-assisted stereoselective synthesisYoann Coquerel, Evelina Colacino, Jean Rodriguez, Jean Martinez and Frédéric LamatyChapter 6: Application of micro reactor methodology for organic synthesisPaul Watts and Charlotte WilesPART 2: STEREOSELECTIVE SYNTHESIS BY BOND FORMATION2.1. STEREOSELECTIVE METHODS FOR C–C BOND FORMATIONChapter 7: Asymmetric α-alkylation of aldehydes, ketones and carboxylic acidsMark C. Kohler, Sarah E. Wengryniuk, and Don M. ColtartChapter 8: Asymmetric aldol reactions in the total syntheses of natural productsSeijiro HosokawaChapter 9: Asymmetric Michael addition and related reactionsPengfei Li, Jun Wang and Fuk Yee KwongChapter 10: Construction of polypropionate fragments in natural product synthesisMaris Turks, Sylvain Laclef and Pierre VogelChapter 11: Organocatalytic conjugate addition in stereoselective synthesisAdrien Quintard and Alexandre AlexakisChapter 12: Stereoselective Nozaki-Hiyama-Kishi reactionPat Guiry and Gráinne HargadenChapter 13: Transition-metal-catalyzed asymmetric C–C cross-couplings in stereoselective synthesis Vasiliki SarliChapter 14: Asymmetric hydroformylation, hydroxy- and alkoxycarbonylation for stereoselective synthesisJamie T. Durrani and Matthew L. ClarkeChapter 15: Intramolecular oxycarbonylation in stereoselective synthesisTibor GraczaChapter 16: Stereoselective cycloaddition reactionsTae-Kyung Lee and Jung-Mo AhnChapter 17: Sigmatropic rearrangements in stereoselective synthesisBrinton Seashore-Ludlow and Peter SomfaiChapter 18: Ring contraction reactions in the total synthesis of biologically active natural productsLuiz F. Silva Jr.Chapter 19: Electrocyclic reactions in stereoselective synthesisMarcus A. TiusChapter 20: Transannular cyclization in natural product total synthesisJiong Yang and Haoran XueChapter 21: Cascade reactions in stereoselective synthesisBor-Cherng Hong and Nitin S. DangeChapter 22: Sulfur dioxide: a powerful tool for the stereoselective construction of C-C bondsPierre Vogel, Dean Markovic and Mâris TurksChapter 23: Transition metal C-H activation: application to stereoselective synthesis of natural products and drugsMickaël Jean and Pierre van de WegheChapter 24: Metathesis reactions in drug and natural product synthesisAkio Saito, Yuji HanzawaChapter 25: Radicals in stereoselective C-C bond formationJosep Bonjoch, Ben Bradshaw and Faïza DiabaChapter 26: Trifluoromethyl (CF3) group insertion methods in stereoselective synthesisTsutomu KonnoChapter 27: Stereoselective organocatalyzed C–C bond-forming reactionsKazuo Nagasawa and Koji YasuiChapter 28: Enzyme-catalysed stereoselective C–C bond formation reactions in total synthesesAdeline Ranoux and Ulf Hanefeld2.2. STEREOSELECTIVE METHODS FOR C–H BOND FORMATIONChapter 29: Stereoselective hydrogenation of C=C bonds: application to drug and natural product synthesisNatalia Andrushko and Vasyl AndrushkoChapter 30: Asymmetric hydrogenation of C=O and C=N bonds in stereoselective synthesisNatalia Andrushko and Vasyl AndrushkoChapter 31: Asymmetric protonation of carbanions and polar double bonds: application to total synthesesThomas Poisson and Shu KobayashiChapter 32: Organocatalytic reduction in stereoselective synthesisFelix Kortmann and Adriaan MinnaardChapter 33: Biocatalytic asymmetric reduction of C=O and activated C=C bonds in stereoselective synthesisTomoko Matsuda, Rio Yamanaka and Kaoru Nakamura2.3. STEREOSELECTIVE METHODS FOR C–O BOND FORMATIONChapter 34: Transition-metal-catalyzed stereoselective oxidations in drug and natural product synthesisAlessandro Scarso and Giorgio StrukulChapter 35: Asymmetric epoxidation in stereoselective synthesisZhicai YangChapter 36: Biocatalytic asymmetric oxidations in stereoselective synthesisAnett Schallmey, Pablo Dominguez de Maria and Paula BraccoChapter 37: Ether transfer methodology: application to the synthesis of polyketide natural productsEric Stefan and Richard E. TaylorChapter 38: Stereoselective formation of 2-deoxyglycosidic bonds in biologically active natural productsDaisuke Takahashi and Kazunobu Toshima2.4. STEREOSELECTIVE METHODS FOR C–N BOND FORMATIONChapter 39: Asymmetric hydroamination and reductive amination in total synthesisManas K. Ghorai, Deo Prakash Tiwari and Aditya BhattacharyyaChapter 40: Carboamination and alkylative cyclization with C-N bond formation in stereoselective synthesesManas K. Ghorai, Sandipan Halder and Sauvik SamantaChapter 41: Cycloadditions with stereoselective C-N bond formation in total synthesesGuillaume Vincent2.5. STEREOSELECTIVE FORMATION OF OTHER C–HETEROATOM AND OTHER BONDSChapter 42: Stereoselective halogenationsChong Kiat Tan, Yi Zhao, Jing Zhou and Ying-Yeung YeungChapter 43: Stereoselective synthesis of halogenated natural productsTakehiko YoshimitsuChapter 44: Asymmetric fluorination methods: application in the stereoselective synthesis of fluorinated drugsVincent Bizet and Dominique CahardChapter 45: Enzymatic halogenation in stereoselective synthesisCormac D. Murphy and Benjamin R. ClarkChapter 46: Stereoselective carbon–sulfur (C–S) bond formationKyungsoo OhChapter 47: Stereoselective methods for carbon-phosphorus (C–P) bond formationMarcin Kalek and Jacek StawinskiChapter 48: Transition-metal-catalyzed asymmetric sulfoxidation in drug and natural product synthesisAlessandro Scarso and Giorgio StrukulPART 3: METHODS OF ANALYSIS AND CHIRAL SEPARATIONChapter 49: NMR-Spectroscopy in drug and natural product analysisStanisuaw Witkowski and Iwona WawerChapter 50: Determination of enantiomeric purity and absolute configuration by NMR spectroscopyThomas J. WenzelChapter 51: Solid-state NMR spectroscopy in drug design and discoveryDavid A. Middleton and Simon G. PatchingChapter 52: Capillary electrophoresis in chiral separationsAns Hendrickx, Debby Mangelings and Yvan Vander HeydenChapter 53: Determination of absolute configuration using chiroptical methodsJoao Marcos Batista, Jr.Chapter 54: Chiral chromatographic methods in the analysis and purification of enantiomersArnau Novell and Cristina MinguillónChapter 55: X-Ray crystallography and 1H NMR anisotropy methods for determination of absolute configurationsNobuyuki HaradaChapter 56: Crystallization based separation of enantiomersYaling Wang and Alex ChenChapter 57: Enzymatic dynamic kinetic resolution in stereoselective synthesisFrancisca Rebolledo, Javier González-Sabín, and Vicente GotorSubject index

“The work will also be very useful to those actively involved in the teaching of modern organic chemistry and synthetic methodologies, because it allows one to quickly compile several examples of applications of methods for a lecture and include details of the corresponding transition states without the need to obtain the original publications.”  (Angew. Chem. Int. Ed, 1 May 2014)