The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis
Allen Y. Hong,Brian M. Stoltz +1 more
TLDR
This microreview outlines key considerations in the application of palladium-catalyzed asymmetric allylic alkylation reactions and presents recent total syntheses of complex natural products that have employed these powerful transformations for the direct, catalytic, enantioselective construction of all-carbon quaternary stereocenters.About:
This article is published in European Journal of Organic Chemistry.The article was published on 2013-05-01 and is currently open access. It has received 275 citations till now. The article focuses on the topics: Enantioselective synthesis & Tsuji–Trost reaction.read more
Citations
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Catalytic enantioselective synthesis of quaternary carbon stereocentres
TL;DR: The many catalytic enantioselective reactions developed during the past decade for the synthesis of single stereoisomers of such organic molecules make it possible to incorporate quaternary stereocentres selectively in many organic molecules that are useful in medicine, agriculture and potentially other areas such as flavouring, fragrances and materials.
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Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis.
TL;DR: This review summarizes innovations and developments in selective organic synthesis that have used cooperative dual catalysis by combining simple aminocatalysts with metal catalysts to address challenging reactions.
Journal ArticleDOI
Selective Carbon–Carbon Bond Cleavage for the Stereoselective Synthesis of Acyclic Systems
TL;DR: It is demonstrated that carbon-carbon bonds have the potential to be a general principle in organic synthesis for the regio-, diastereo-, and even enantioselective preparation of adducts despite the fact that C-C single bonds are among the least reactive functional groups.
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Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.
Martin Büschleb,Stéphane Dorich,Stephen Hanessian,Daniel Tao,Kyle B. Schenthal,Larry E. Overman +5 more
TL;DR: Emphasis has been put on methods to create quaternary carbon stereocenters, including syntheses of the same natural product by different groups, thereby showcasing the diversity of thought and individual creativity.
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All-Carbon Quaternary Stereogenic Centers in Acyclic Systems through the Creation of Several C–C Bonds per Chemical Step
TL;DR: This Perspective presents approaches that tackle the stimulating problem of efficiency while answering interesting synthetic challenges and describes how to create all-carbon quaternary stereogenic centers via the creation of several new carbon-carbon bonds in an acyclic system and in a single-pot operation from simple precursors.
References
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Journal ArticleDOI
Asymmetric Transition Metal-Catalyzed Allylic Alkylations.
TL;DR: The focus of this review is on the area of enantioselective transition metal-catalyzed allylic alkylations which may involve C-C as well as C-X (X ) H or heteroatom) bond formation.
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Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.
TL;DR: Alkylations with Phenols, Nitrogen Nucleophiles in AAA Total Synthesis, and Considerations for Enantioselective Allylic Alkylation are presented.
Journal ArticleDOI
Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions
TL;DR: Transition metal catalyzed decarboxylative allylation, benzylations, and interceptive allylations are reviewed.
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Catalytic enantioselective construction of all-carbon quaternary stereocenters
Barry M. Trost,Chunhui Jiang +1 more
TL;DR: In this paper, a comprehensive account of the currently available methods of the above transformation that afford high enantioselectivities and synthetically useful yields is given. But this review is limited to all-carbon quaternary stereocenters, i.e. carbon atoms bearing four different carbon substituents.
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.
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Catalytic enantioselective construction of all-carbon quaternary stereocenters
Barry M. Trost,Chunhui Jiang +1 more