Journal ArticleDOI
Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.
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TLDR
Research by this group on the development and understanding of enantioselective versions of the Diels-Alder reactions is described, based on presentations given first at the University of Cologne, Germany, then at the Roger Adams Award Symposium, and later at the Bürgenstock Conference of 2001.Abstract:
One hundred years after the birth of Kurt Alder and seventy-five years after the discovery of his famous reaction, one of the most important and fascinating transformations in chemistry, research on that process continues to surprise, excite, delight, and inform the chemical community. This article is based on presentations given first at the University of Cologne, Germany (Kurt Alder lecture, 1992), then at the Roger Adams Award Symposium (1993), and later at the Burgenstock Conference of 2001, and describes research by our group on the development and understanding of enantioselective versions of the Diels-Alder reactions. The elements of this review include (1) development of new chiral Lewis acid catalysts for highly enantioselective (>25:1) [4+2] cycloadditions; (2) the fine mechanistic details and pre-transition-state assemblies of these reactions; (3) the fundamental understanding of catalytic activity and enantioselectivity for highly enantioselective Diels-Alder processes; and (4) applications to the synthesis of complex molecules. The range and power of the Diels-Alder reaction have steadily increased over seven decades. The end of this remarkable development is not in sight, a high compliment to this field of Science and to its great inventor.read more
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Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates
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Diphenylprolinol Silyl Ethers as Efficient Organocatalysts for the Asymmetric Michael Reaction of Aldehydes and Nitroalkenes
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Click Chemistry beyond Metal-Catalyzed Cycloaddition
TL;DR: This Minireview discusses the success and applicability of new, in particular metal-free, click reactions, which expand the opportunities for synthesizing small organic compounds as well as tailor-made macromolecules and bioconjugates.
Journal ArticleDOI
Catalytic asymmetric synthesis of all-carbon quaternary stereocenters
TL;DR: Only a few catalytic asymmetric C-C bond-forming reactions have been shown to be useful for constructing all-carbon quaternary stereocenters and this Perspective examines the current state of such methods.
Journal ArticleDOI
Catalytic Asymmetric Synthesis of α-Amino Acids
Carmen Nájera,José M. Sansano +1 more
References
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Book
Catalytic Asymmetric Synthesis
TL;DR: Asymmetric Hydrogenation (T. Ohkuma, et al. as discussed by the authors ), asymmetric carbon-Carbon Bond-Forming Reactions (K. Nozaki & I. Negishi). Asymmetric Addition and Insertion Reactions of Catalytically-Generated Metal Carbenes (M. O'Donnell), and asymptotic phase-transfer Reactions.
Book
Asymmetric catalysis in organic synthesis
TL;DR: In this article, the authors present a textbook of practical organic chemistry with Electronic Structure Methods (ESM) for HPLC and HPLC-based problem solving in organic synthesis.
Journal ArticleDOI
Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications
Journal ArticleDOI
Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method.
E. J. Corey,Christopher J. Helal +1 more
TL;DR: High enantioselectivity can be achieved when chiral oxazaborolidines are used as catalysts in the reduction of ketones by borane when the two reactants are activated and held in close proximity by the catalyst.