Asymmetric Synthesis of Three-Membered Rings

Name: Asymmetric Synthesis of Three-Membered Rings
Brand: Wiley-VCH
Price: 160.99 EUR
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Hélène Pellissier Alessandra Lattanzi Renato Dalpozzo(Autor*in)

Wiley-VCH (Verlag)

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Erschienen am 28. März 2017

XVI, 590 Seiten

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Hélène Pellissier is currently Chargée de Recherche (CNRS) at Aix Marseille Université (France). She carried out her PhD under the supervision of Dr G. Gil in Marseille in 1987. After a postdoctoral period in Professor K. P. C. Vollhardt´s group at the University of California, Berkeley (USA), she joined the group of Professor M. Santelli in Marseille in 1992. She is the author of 95 papers including reviews in international journals, 7 books, and 6 book chapters.

Alessandra Lattanzi obtained the national Italian habilitation for Full Professor in organic chemistry in 2013 at the University of Salerno (Italy) and received her MSc and PhD from University of Rome "La Sapienza" (Italy). From 1999 to 2000 she was a visiting scientist in Prof. V. K. Aggarwal's group in Sheffield (UK). In 2005, she was promoted to Associate Professor at the University of Salerno. She has authored over 95 publications including reviews in international journals, 12 book chapters in the areas of stereoselective synthesis of heterocyclic compounds and oxidation reactions.

Starting in 1983, Renato Dalpozzo was a Researcher of Organic Chemistry at the University of Bologna (Italy). In 1992, he moved to the University of Calabria (Italy) as Associate Professor of Organic Chemistry and then as Full Professor of Organic Chemistry. For ten years he was also full Professor of Environmental and Cultural Heritage Chemistry. He has authored over 110 publications and a book chapter in the areas of the reactivity of organometallic compounds with aromatic systems, the use of dianions derived from enamino carbonyl compounds, the stereoselective reduction of various classes of ketones, the development of new Lewis acid systems, and enantioselective organocatalysis. He authored also a text book for students of his University.

Autor*in

Hélène Pellissier

Aix Marseille Université, France

Alessandra Lattanzi

Aix Marseille Université, France

Renato Dalpozzo

Aix Marseille Université, France

Inhalt

CHAPTER 1: Asymmetric Cyclopropanations
1. Introduction
2. Simmons-Smith Cyclopropanation
3. Transition-Metal-Catalyzed Decomposition of Diazoalkanes
4. Michael-Initiated Ring Closure (MIRC)
5. Miscellaneous
6. Conclusion
CHAPTER 2: Asymmetric Aziridinations
1. Introduction
2. Aziridination Based on the Use of Chiral Substrates
3. Aziridination Based on the Use of Chiral Catalysts
4. Conclusion
CHAPTER 3: Asymmetric Epoxidations
1. Introduction
2. Epoxidation using Chiral Metal Catalysts
3. Epoxidation using Chiral Organocatalysts
4. Kinetic Resolutions
5. Epoxidation using Chiral Sulfur Ylides
6. Darzens Reaction
7. Conclusion
CHAPTER 4: Asymmetric Oxaziridinations
1. Introduction
2. Oxaziridination using Chiral Substrates
3. Oxaziridination using Chiral Catalysts
4. Kinetic Resolutions
5. Conclusion
General Conclusion

List of Abbreviations

2,6-DCPNO 2,6-dichloropyridine N-oxide acac acetylacetonate ACDC asymmetric counteranion-directed catalysis Ad 1-adamantyl AKR aminolytic kinetic resolution Anth anthryl Ar aryl BARF tetrakis(3,5-bis(trifluoromethyl)phenyl)borate BHT 2,6-di-t-butyl-4-methylphenyl BINAM 1,1´-binaphthyl-2,2´-diamine BINAP 2,2´-bis(diphenylphosphino)-1,1´- binaphthyl BINOL 1,1´-bi-2-naphthol BMEH Bacillus megaterium epoxide hydrolase Bn benzyl Boc tert-butoxycarbonyl Box bis(oxazoline) Bs benzenesulfonyl Bt benzotriazole BUDAM tetra-tert-butyldianisylmethyl Bz benzoyl (PhCO) CAN ceric ammonium nitrate CBS oxazaborolidine Corey-Bakshi-Shibata catalyst Cbz benzyloxycarbonyl CHP cumyl hydroperoxide Cod 1,5-cyclooctadiene Cp cyclopentadienyl CPO chloroperoxidase CSA camphorsulfonic acid Cy cyclohexyl DABCO 1,4-diazabicyclo[2.2.2]octane DAM dianisylmethyl DAP diaminopimelic acid DBN 3,5-dinitrobenzoyl DBU 1,5-diazabicyclo[5.4.0]undec-5-ene DCC N,N´-dicyclohexylcarbodiimide DCE 1,2-dichloroethane de diastereomeric excess DEAD diethyl azodicarboxylate Dec decyl DFT density functional theory DIAD diisopropyl azodicarboxylate DIC diisopropylcarbodiimide DIPEA diisopropyl ethyl amine DMAP 4-(N,N-dimethylamino)pyridine DMD dimethyl dioxirane DME dimethoxyethane DMF N,N-dimethylformamide DMM dimethoxymethane DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone DMSO dimethylsulfoxide DNA deoxyribonucleic acid DPPA diphenylphosphoryl azide dr diastereomeric ratio E electrophile EDA ethyl diazoacetate ee enantiomeric excess EH epoxide hydrolase EPR electron paramagnetic resonance ESI-MS electrospray ionization-mass spectrometry Esp a,a,a´,a´-tetramethyl-1,3-benzenedipropionate EWG electron-withdrawing group FAD flavin adenine dinucleotide FG functional group Fu furyl GDH glucose dehydrogenase HDHH halohydrin dehalogenase Hept heptyl Hex hexyl HKR hydrolytic kinetic resolution HMDS hexamethyldisilazide HMPA hexamethylphosphoramine JHC Jørgensen-Hayashi catalyst KSAE Katsuki-Sharpless asymmetric epoxidation L ligand LA Lewis acid LDA lithium diisopropylamide LDHs layered double hydroxides l-DET l-diethyl tartrate l-DIPT l-diisopropyl tartrate LEH limonene 1,2-epoxide hydrolase LG leaving group LIDAKOR lithium diisopropylamide-potassium t-butoxide LTMP lithium 2,2,6,6-tetramethylpiperidine M metal MCPBA 3-chloroperoxybenzoic acid MEDAM tetramethyldianisylmethyl MEDPM tetramethyldiphenylmethyl MEM methoxyethoxymethyl MEOX methyl 1-oxo-(2-oxazolidine)-4-carboxylate MEPY methyl 2-oxopyrrolidine-5-carboxylate Mes mesyl MIB morpholino isoborneol MIRC Michael-initiated ring-closure MOM methoxymethyl Ms mesyl (MeSO2) MS molecular sieves MSH O-mesitylenesulfonylhydroxylamine MTBD 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene Mts 2,4,6-trimethylphenylsulfonyl NADH dihydronicotinamide adenine dinucleotide NADPH nicotinamide adenine dinucleotide phosphate Naph naphthyl NBS N-bromosuccinimide NCS N-chlorosuccinimide NMP N-methyl pyrrolidinone NOBIN 1-amino-1´-hydroxylbinaphthyl Non nonyl Npt naphthyl Ns nosyl NsNIPh [(nosylimino)iodo]benzene Nttl 1,8-naphthanoyl-tert-leucine Nu nucleophile Oct octyl PEG polyethylene glycol Pf phenylfluorenyl Pfm perfluorobutyramide PG protecting group Phen phenanthryl Phth phthaloyl Piv pivaloyl (t-BuCO) PLA poly-l-alanine PLL poly-l-leucine PMB 4-methoxybenzyl PMP 4-methoxyphenyl PNB para-nitrobenzyl PNNP N,N´-bis[o-(diphenylphosphino)-benzylidene]cyclohexane-1,2-diamine PPTS pyridinium p-toluenesulfonate PTAB phenyltrimethylammonium tribromide PTC phase-transfer catalyst PTFE polytetrafluoroethylene Py pyridyl Pybox pyridylbis(oxazoline) r.t. room temperature Salen salicylidenethanediamine Segphos 5,5´-bis(diphenylphosphino)-4,4´-bi-1,3-benzodioxole SEM 2-(trimethylsilyl)ethoxymethyl Ses trimethylsilylethanesulfonyl SIPr N,N´-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene SMO styrene monooxygenase SPC sodium...

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