Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction.
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TLDR
The design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Brønsted base/H-bond-donor organocatalysts are reported, which allow the enantioselective construction of β-nitroamines possessing a fully substituted carbon atom.Abstract:
The design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Bronsted base/H-bond-donor organocatalysts are reported. These catalysts incorporate a triaryliminophosphorane as the Bronsted basic moiety and are readily synthesized via a last step Staudinger reaction of a chiral organoazide and a triarylphosphine. Their application to the first general enantioselective organocatalytic nitro-Mannich reaction of nitromethane to unactivated ketone-derived imines allows the enantioselective construction of β-nitroamines possessing a fully substituted carbon atom. The reaction is amenable to multigram scale-up, and the products are useful for the synthesis of enantiopure 1,2-diamine and α-amino acid derivatives.read more
Citations
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Journal ArticleDOI
Chiral Iminophosphoranes-An Emerging Class of Superbase Organocatalysts.
TL;DR: Recent progress in the field of chiral iminophosphorane superbase organocatalysis is summarized and catalysts design, different approaches to their synthesis, and applications in asymmetric synthesis are outlined and discussed in detail.
Journal ArticleDOI
Bifunctional Iminophosphorane Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α-Substituted Acrylate Esters.
TL;DR: The highly enantioselective sulfa-Michael addition of alkyl thiols to unactivated α-substituted acrylate esters catalyzed by a bifunctional iminophosphorane organocatalyst under mild conditions is described.
Journal ArticleDOI
Asymmetric Synthesis of Quaternary α‐Amino Acids and Their Phosphonate Analogues
TL;DR: This Focus Review provides a summary of recent approaches to catalytic asymmetric synthesis of quaternary α-amino acids and α-aminophosphonates.
Journal ArticleDOI
Synergetic Organocatalysis for Eliminating Epimerization in Ring-Opening Polymerizations Enables Synthesis of Stereoregular Isotactic Polyester.
Maosheng Li,Yue Tao,Yue Tao,Jiadong Tang,Jiadong Tang,Yanchao Wang,Yanchao Wang,Xiaoyong Zhang,Youhua Tao,Xianhong Wang +9 more
TL;DR: An effective bifunctional single-molecule organocatalysis for selective ring-opening polymerization of OCAs without epimerization is described, allowing sustainable and scalable synthesis of a stereoregular functional polyester.
References
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Journal ArticleDOI
In the Golden Age of Organocatalysis
Peter I. Dalko,Lionel Moisan +1 more
TL;DR: The diverse examples show that in recent years organocatalysis has developed within organic chemistry into its own subdiscipline, whose "Golden Age" has already dawned.
Journal ArticleDOI
Small-molecule H-bond donors in asymmetric catalysis.
Journal ArticleDOI
Asymmetric catalysis by chiral hydrogen-bond donors.
Mark S. Taylor,Eric N. Jacobsen +1 more
TL;DR: This review documents the structural and mechanistic features that contribute to high enantioselectivity in hydrogen-bond-mediated catalytic processes in small-molecule, synthetic catalyst systems.
Book
Comprehensive organic synthesis
Paul Knochel,Gary A. Molander +1 more
TL;DR: Synthetic chemists requiring the essential facts in new areas, as well as students completely new to the field, will find "Comprehensive Organic Synthesis, Second Edition" an invaluable source, providing an authoritative overview of core concepts.