Asymmetric Synthesis II (eBook)

Mathias Christmann studied chemistry at the Technical University of Braunschweig and received a PhD from the Leibniz University of Hannover with Markus Kalesse. After a postdoctoral research with Craig J. Forsyth at the University of Minnesota, he started his independent career at the RWTH Aachen as a Liebig-Fellow of the Fonds der Chemischen Industrie. Since 2008, Christmann is an Associate Professor at the Technical University of Dortmund working in the areas of organocatalysis, natural products synthesis and sustainable chemistry. Stefan Bräse studied chemistry in Bangor, UK, Marseille, France, and Göttingen, Germany, where he gained his doctorate under Armin de Meijere in 1995. After post-doctoral appointments at Uppsala University, Sweden under J.-E. Bäckvall and The Scripps Research Institute, La Jolla, USA with K. C. Nicolaou, he began his research career at the RWTH Aachen with Dieter Enders in 1997, obtaining his lecturing qualification in 2001. He became a professor at the University of Bonn that same year and since 2003 he has been Full Professor at the Karlsruhe Institute of Technology. Professor Bräse has more than 250 publications to his name and is a recipient of the ORCHEM award. His research interests include methods in drug discovery, combinatorial chemistry with a focus on the synthesis of biologically active compounds, total synthesis of natural products and nanotechnology.

CATALYTIC ENANTIOSELECTIVE ALKYLATION OF PROCHIRAL KETONE ENOLATES
Background
Strategy and Results
Asymmetric Allylic Alkylation in Total Synthesis
Conclusions

POINT-TO-PLANAR CHIRALITY TRANSFER IN TOTAL SYNTHESIS: SCALABLE AND PROGRAMMABLE SYNTHESIS OF HAOUAMINE A AND ITS ATROPISOMER
Introduction
Synthetic Strategy Featuring Point-to-Planar Chirality Transfer
Programmable Synthesis of Haouamine A and Its Atropisomer

TETHERED AMINOHYDROXYLATION
Introduction and Background
Tethered Aminohydroxylation
Amide-Based Reoxidants
Evidence for the Mechanism of the TA Reaction
Applications in Organic Synthesis
Conclusion and Future Work

ORGANOCATALYZED TRANSFORMATIONS OF A, B-UNSATURATED CARBONYL COMPOUNDS THROUGH IMINIUM ION INTERMEDIATES

THE RENAISSANCE OF SILICON-STEREOGENIC SILANES: A PERSONAL ACCOUNT
Background
Results
Conclusion

ASYMMETRIC DIENAMINE ACTIVATION
Introduction
Historic Background
Results
Conclusion

ASYMMETRIC BRØNSTED ACID CATALYSIS
Introduction and Background
Strategy
Results
Summary

QUATERNARY STEREOGENIC CENTERS BY ENANTIOSELECTIVE B-CARBON ELIMINATIONS FROM TERT-CYCLOBUTANOLS
Background
Objective: Enantioselective Formation of Quaternary Stereogenic Centers in Combination with Reactive Alkyl-Rhodium
Intermediates
Selective Generation of the Alkyl-Rhodium Species and Its Downstream Reactivities

TOTAL SYNTHESIS OF OSELTAMIVIR AND ABT-341 USING ONE-POT TECHNOLOGY
Introduction
Results
Conclusions

ENANTIOSELECTIVE ANNULATIONS WITH CHIRAL N-MESITYL N-HETEROCYCLIC CARBENES
Introduction
Catalytic Generation of Chiral Enolate Equivalents
Catalytic Generation of Homoenolate Equivalents
Enantioselective Cascade Reactions Catalyzed by Chiral N-Heterocyclic Carbenes
Catalytic Annulations via a, ß-Unsaturated Acyl Azoliums
Conclusions

ASYMMETRIC COUNTERANION-DIRECTED CATALYSIS (ACDC)
Concept
Application of ACDC to Organocatalysis
Application of ACDC to Transition Metal Catalysis
Application of ACDC to Lewis Acid Catalysis

ENANTIOSELECTIVE ORGANO-SOMO CATALYSIS: A NOVEL ACTIVATION MODE FOR ASYMMETRIC SYNTHESIS
Background
Objective
Results

ENANTIOSELECTIVE PASSERINI REACTION
Introduction
Background
Results
Conclusion and Perspective

RAPID ENANTIOMERIC EXCESS DETERMINATION

ASYMMETRIC CATALYSIS OF REVERSIBLE REACTIONS
Thermochemistry of Asymmetric Catalyses Close to the Equilibrium
Kinetic Modeling of a Reversible Asymmetric Catalytic Reaction
Case Study: a Reversible Asymmetric Organocatalytic Reaction
Conclusions

EXPLOITING FLUORINE CONFORMATIONAL EFFECTS IN ORGANOCATALYST DESIGN: THE FLUORINE?IMINIUM ION GAUCHE EFFECT

DUTCH RESOLUTION

CONSTRUCTION OF ANTI-ME-OH VICINAL RELATIONSHIPS IN POLYKETIDES
Introduction
Marshall - Tamaru Reaction
Conclusions

PHOTOSWITCHABLE GENERAL BASE CATALYSTS
Introduction and Background
Strategy and Results
Outlook

ASYMMETRIC HALONIUM ADDITION TO OLEFINS
Introduction
Intramolecular Lactonizations, Etherifications, and Aminations
Polyene Cyclizations
Intermolecular Additions to Alkenes
Conclusion

CATALYTIC ASYMMETRIC GOSTELI - CLAISEN REARRANGEMENT (CAGC)

BIOMIMETIC TOTAL SYNTHESIS OF THE PENIFULVIN FAMILY
Introduction
The Penifulvin Family: Isolation and Biogenetic Origin
Total Syntheses of Penifulvins A, B, and C
Summary

CATALYST-CONTROLLED 1,3-POLYOL SYNTHESES

ENANTIOSELECTIVE CARBONYL ALLYLATION AND CROTYLATION FROM THE ALCOHOL OXIDATION LEVEL VIA C?C BOND FORMING TRANSFER HYDROGENATION
Introduction and Background
Strategy
Results

STEREOSELECTIVE SYNTHESIS WITH HYPERVALENT IODINE REAGENTS

ASYMMETRIC GOLD-CATALYZED REACTIONS
Introduction
Diphosphine-Gold Complexes in Enantioselective Catalysis
Monophosphine-Gold Complexes in Enantioselective Catalysis

ASYMMETRIC CATALYSIS IN THE TOTAL SYNTHESIS OF LIPIDS AND POLYKETIDES
Background
Tuberculostearic Acid: One Isolated Methyl Group
Ant Pheromones: Vicinal Methyl Branches
Deoxypropionates: 1,3-Methyl Arrays
Membrane-Spanning Lipids: