Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: asymmetric formal synthesis of (-)-metazocine.

doi:10.1021/OL702019B

Paper

Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: asymmetric formal synthesis of (-)-metazocine.

Published Sep 26, 2007 · M. Anada, Masahiko Tanaka, Takuya Washio

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Abstract

Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate], Rh2(S-TFPTTL)4, is an exceptionally efficient catalyst for enantioselective aminations of silyl enol ethers derived from acyclic ketones or alpha,beta-enones with [N-(2-nitrophenylsulfonyl)imino]phenyliodinane (NsN=IPh), providing N-(2-nitrophenylsulfonyl)-alpha-amino ketones in high yields and with enantioselectivities of up to 95% ee. The effectiveness of the present catalytic protocol has been demonstrated by an asymmetric formal synthesis of (-)-metazocine.

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Dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate] effectively catalyzes enantioselective amination of silyl enol ethers, providing

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Catalytic enantioselective amination of silyl enol ethers using chiral dirhodium(II) carboxylates: asymmetric formal synthesis of (-)-metazocine.

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References

Citations

A Cooperative Cobalt-Driven System for One-Carbon Extension in the Synthesis of (Z)-Silyl Enol Ethers from Aldehydes: Unlocking Regio- and Stereoselectivity

This cobalt-based catalytic system efficiently synthesizes (Z)-silyl enol ethers from aldehydes, overcoming challenges like additive use and extreme reaction temperatures.

Catalytic, asymmetric carbon–nitrogen bond formation using metal nitrenoids: from metal–ligand complexes via metalloporphyrins to enzymes

Metal nitrenoid chemistry offers efficient and selective nitrogen atom introduction into small molecules, with diverse catalysts and metals available for enantioselective reactions.

Aspartyl β-Turn-Based Dirhodium(II) Metallopeptides for Benzylic C(sp3)-H Amination: Enantioselectivity and X-ray Structural Analysis.

This new class of peptide-based dirhodium(II) complexes offers high enantioselectivity and can efficiently generate new chiral dirhodium(II) catalyst libraries for various organic reactions.

Catalytic Enantioselective Amination of Enol Silyl Ethers Using a Chiral Paddle-Wheel Diruthenium Complex.

The chiral paddle-wheel dinuclear ruthenium catalyst effectively catalyzes enantioselective amination of enol silyl ethers, resulting in up to 97% enantioselectivity compared to rhodium catalysts

Iridium-Catalyzed Amidation of In Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters.

Iridium-catalyzed amidation of silyl ketene acetals allows facile access to -amido esters, making it a convenient method for preparing -aryl and -alkyl esters.