Synthesis of<i>N</i>-aryl β-amino acid derivatives<i>via</i>Cu(<scp>ii</scp>)-catalyzed asymmetric 1,4-reduction in air

Li, Min; Xia, Hong-Feng; Liu, Yang; Hong, Tao; Xie, Lin‐Jie; Li, Shijun; Wu, Jing

doi:10.1039/c9ra01203f

Cited by 14 publications

(3 citation statements)

References 68 publications

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“…For example, Wu and co-workers showed that both β-amido and anilido substituents give access to different chiral βamino esters 13 in generally high yields and enantioselectivity (Figure 6). [48][49][50] The best ligands for this class of substrates were shown to be L7 or L10, depending on the Nsubstitution. Similarly, the Buchwald group showed in 2004 that the reduction of β-azaheterocyclic unsaturated esters is feasible using L6 (Figure 6).…”

Section: αβ-Unsaturated Esters Amides and Acidsmentioning

confidence: 99%

Catalytic Asymmetric Conjugate Reduction

et al. 2023

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Enantioselective reduction reactions are privileged transformations for the construction of trisubstituted stereogenic centers. While these include established synthetic strategies, such as asymmetric hydrogenation, methods based on the enantioselective addition of hydridic reagents to electrophilic prochiral substrates have also gained importance. In this context, the asymmetric conjugate reduction (ACR) of α,β-unsaturated compounds has become a convenient approach for the synthesis of chiral compounds with trisubstituted stereocenters in α-, β-, or γ-position to electron-withdrawing functional groups. Because such activating groups are diverse and amenable of further derivatizations, ACRs provide a general and powerful synthetic entry towards a variety of valuable chiral building blocks. This Review provides a comprehensive collection of catalytic ACR methods involving transition-metal, organic, and enzymatic catalysis since its first versions dating back to the late 1970s.

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Section: αβ-Unsaturated Esters Amides and Acidsmentioning

confidence: 99%

Catalytic Asymmetric Conjugate Reduction

et al. 2023

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“…[44] The development of synthetic approaches to β-amino ketones, β-amino sulfones, β-amino acids and their derivatives (esters and nitriles) bearing arylamine moiety has a special importance because of their numerous applications to divers functional materials, drugs and analogs of natural products. [45,46] Arylamines are generally viewed as relatively poor nucleophiles toward electrophiles, including Michael acceptors, especially ones bearing internal carbon-carbon double bond. Therefore, it is reasonable to assume that for success, their reactions with electron-deficient alkenes should require an additive (catalyst) that can increase their reactivity.…”

Section: Non-catalyzed Conjugate Nucleophilic Addition Of Aminesmentioning

confidence: 99%

Aza‐Michael Reaction: A Decade Later – Is the Research Over?

Rulev

2023

Eur J Org Chem

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The 1,4‐conjugated addition of nitrogen centered nucleophiles to electron‐deficient alkenes, historically called the aza‐Michael addition, is one of the most significant and widely used reactions in modern synthetic organic chemistry. In the last decade, great progress has been made in this field namely in the development of various catalytic systems. Fundamental advances involve the use of transition metal catalysts, organocatalysts, enzymes, ionic liquids, Brønsted and Lewis acids and bases. This Review aims to critically analyze the results of research into the reactions of aliphatic and aromatic amines with Michael acceptors.

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“…Wu et al presented an interesting approach to exploiting prochiral precursors to produce β-amino acid esters by developing enantioselective conjugate reductions of (βarylamino)-β-alkyl or β-arylacrylates. 114 The reaction was accomplished with a PMHS-derived CuH-catalysis system and (S)-SEGPHOS (S)-L2. Various alkyl and aryl-substituted substrates produced excellent results (Scheme 113 and Scheme 114).…”

Section: Asymmetric Reduction Of αβ-Unsaturatedmentioning

confidence: 99%

Organosilanes in Metal-Catalyzed, Enantioselective Reductions

Larson

Liberatore

2021

Org. Process Res. Dev.

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The growth and development of an extensive range of metals complexed with chiral ligands for the purpose of catalyzing a variety of reactions in an enantioselective manner has been impressive for its scope, chemical yields and high ee values. Chief among the classes of synthetic transformations has been that of the asymmetric reduction of prochiral substrates. These include the asymmetric reduction of prochiral ketones, imines, unsaturated aldehydes, ketones, esters, nitriles and olefins, as well as a number of asymmetric coupling reactions. In concert with these efficient catalyst systems, organosilanes have the ability to carry out any number of organic reductions under a variety of conditions. In these reactions, which in reality are hydrosilylations (hydrosilylation and reduction are considered interchangeable herein) in which the initially resulting silylated product is hydrolyzed to the ultimate desired functionality, the ability to sterically and electronically alter the organosilane reductant can contribute to the overall success of the transformation. In this review, we present a thorough compilation of the literature covering the use of organosilanes in metal-catalyzed asymmetric reductions (hydrosilylations) and coupling reactions.

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Synthesis ofN-aryl β-amino acid derivativesviaCu(ii)-catalyzed asymmetric 1,4-reduction in air

Abstract: Non-precious metal copper-catalyzed asymmetric 1,4-hydrosilylation of β-aryl or β-alkyl-substituted N-aryl β-enamino esters proceeded in air in high yields and excellent enantioselectivities (26 examples, 90–98% ee).

Cited by 14 publications

References 68 publications

Catalytic Asymmetric Conjugate Reduction

Catalytic Asymmetric Conjugate Reduction

Aza‐Michael Reaction: A Decade Later – Is the Research Over?

Organosilanes in Metal-Catalyzed, Enantioselective Reductions

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