Asymmetric three-component Strecker reactions catalyzed by trans-4-hydroxy-L-proline-derived N,N'-dioxides.

doi:10.1002/chem.200800319

Paper

Asymmetric three-component Strecker reactions catalyzed by trans-4-hydroxy-L-proline-derived N,N'-dioxides.

Published Jul 28, 2008 · Y. Wen, B. Gao, Yingzi Fu

Chemistry

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Abstract

Novel trans-4-hydroxy-L-proline-derived N,N'-dioxides have been developed and used as efficient organocatalysts for the one-pot three-component Strecker reaction with an aldehyde, (1,1-diphenyl)methylamine, and TMSCN. Both aromatic and aliphatic aldehydes were found to be suitable substrates. The corresponding alpha-amino nitriles were obtained in high yields with up to 95 % ee (ee=enantiomeric excess) under mild conditions. Optically pure products could be obtained after a single recrystallization. The catalyst can be easily prepared from trans-4-hydroxy-L-proline and a diamine in three steps. Based on the experimental results and the observed absolute configurations of the products, a possible transition state has been proposed to explain the origin of the asymmetric induction.

Study Snapshot

Trans-4-hydroxy-L-proline-derived N,N'-dioxides effectively catalyze one-pot Strecker reactions, resulting in high yields of alpha-amino nitriles with up to 95% ee under mild conditions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Asymmetric three-component Strecker reactions catalyzed by trans-4-hydroxy-L-proline-derived N,N'-dioxides.

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References

Enantioselective Strecker Reaction Promoted by Chiral N-Oxides

Chiral N-oxides can promote the Strecker reaction, leading to enantioselective a-amino nitriles with up to 73% enantioselectivity, especially for electron-deficient aldimines under mild conditions.

Highly enantioselective strecker reaction of ketoimines catalyzed by an organocatalyst from (S)-BINOL and L-prolinamide.

The novel organocatalyst from (S)-BINOL and L-prolinamide effectively catalyzes the Strecker reaction of ketoimines, providing highly enantioselective synthesis of pharmaceutically important disubstituted a-amino nit

Asymmetric Ring Opening of meso-Epoxides with Aromatic Amines Catalyzed by a New Proline-Based N,N'-Dioxide-Indium Tris(triflate) Complex

The new proline-based N,N'-dioxide-indium tris(triflate) complex catalyzes asymmetric ring opening of meso-epoxides with aromatic amines in high yields and excellent enantioselectivity, providing a

Asymmetric Strecker Reaction of N‐Benzhydrylimines Utilising New Tropos Biphenyldiol‐Based Ligands

Two privileged ligands identified in this study provide superior results in the Strecker-type reaction of N-benzhydrylimines, with a correlation between ee values and diastereomeric ratio.

Highly Enantioselective Allylation of Aromatic α‐Keto Phosphonates Catalyzed by Chiral N,N′‐Dioxide‐Indium(III) Complexes

The chiral N,N′-dioxide-3g-indium(III) complex efficiently catalyzes the allylation of aromatic -keto phosphonates, resulting in high yields and enantioselectivity up to 91%.

Enantioselective aza-Diels-Alder reaction of aldimines with "Danishefsky-type diene" catalyzed by chiral scandium(III)-N,N'-dioxide complexes.

Chiral scandium(III)-N,N'-dioxide complexes catalyze the enantioselective aza-Diels-Alder reaction between 1,3-butadiene and aldimines, yielding 2,5-disubstituted

Citations

Bipyridine-N,N'-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues.

This study developed a novel chiral C2-symmetric bipyridine-N,N'-dioxides catalyst for asymmetric synthesis of 1H-Pyrazolo[3,4-b]pyridine analogues with 85-97% yield and up to 99% enantios

Metabolic engineering strategy for synthetizing trans-4-hydroxy-l-proline in microorganisms

Metabolic engineering advances have improved the production of trans- 4-hydroxy-l-proline in microorganisms, addressing production challenges and enhancing pharmaceutical applications.

The Ketone-Amine-Alkyne (KA2) coupling reaction: Transition metal-catalyzed synthesis of quaternary propargylamines

The KA2 coupling reaction offers a greener, one-step synthetic method for quaternary propargylamines, requiring simple, widely-available starting materials and reducing time and environmental impact compared to conventional approaches.

Organocatalysts Derived from Unnatural α-Amino Acids: Scope and Applications.

Organocatalysts derived from unnatural -amino acids enable efficient and stereoselective synthesis of complex natural products through covalent interactions that raise or lower the HOMO or LUMO levels.

Organocatalytic Enantioselective Strecker Reaction with Seven-Membered Cyclic Imines

The Strecker reaction with seven-membered cyclic imines is an organocatalytic enantioselective method for synthesis of cyclic compounds with high selectivity.

Strecker reaction and α-amino nitriles: Recent advances in their chemistry, synthesis, and biological properties

Recent advances in -amino nitrile chemistry, synthesis, and biological properties have led to the development of new anti-hyperglycemic drugs and promising pharmacological and agrochemical agents.