Synergistic Cu/Pd Catalysis for Enantioselective Allylic Alkylation of Aldimine Esters: Access to α,α‐Disubstituted α‐Amino Acids

Wei, Liang; Xu, Shiming; Zhu, Qiao; Che, Chao; Wang, Chun‐Jiang

doi:10.1002/ange.201707019

Cited by 36 publications

(1 citation statement)

References 74 publications

(16 reference statements)

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“…57 Comprehensive computational studies were carried out by Houk and co-workers 58 to explore the origin of regio-and stereoselectivities of Wang's synergistic Cu/Ir catalysis and their previous Cu/Pd catalysis. 59 Computational models and distortion/interaction analyses has identified versatile modes of stereoinduction wherein the copper azomethine ylide species can face-selectively intercept metal-π-allyl intermediates utilizing attractive dispersion interactions and/or sterically caused (Scheme 24). Hartwig and co-workers disclosed bidentate azaaryl acetamides and acetates 87 to be viable prochiral enolates with the aid of chiral copper catalyst Cu(I)/L25 (Scheme 25).…”

Section: Lewis Acid/irmentioning

confidence: 99%

Synergistic Dual Catalysis in Stereodivergent Synthesis

Wei,

Fu,

Wang

et al. 2024

ACS Catal.

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Chiral skeletons with multiple stereogenic centers widely reside in nature and drugs, and their relative and absolute configuration often determine their physiological or pharmacological properties. Stereodivergent synthesis of chiral molecules is not only of great significance, but also is highly challenging since the formation of one of the diastereomers is inherently preferred in most asymmetric reactions. Stereodivergent dual catalysis, introduced in 2013 by the Carreira group, perfectly catered to all the requirements for full stereoselectivity control of given reactions since two chiral catalysts are utilized in a synergistic way and act independently, and has now been arguably the most efficient strategy to realize stereodivergent synthesis. This comprehensive review presents an overview of the development of stereodivergent synthesis enabled by synergistic dual catalysis in the past ten years, providing readers with the fundamental attributes as well as the ability, scope, mechanism, as well as limitations of this strategy.

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Section: Lewis Acid/irmentioning

confidence: 99%

Synergistic Dual Catalysis in Stereodivergent Synthesis

Wei,

Fu,

Wang

et al. 2024

ACS Catal.

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Chemo‐selective Rh(II)/Pd(0) Dual Catalysis: Synthesis of All‐Carbon C3‐Quaternary Allylic Oxindoles from N‐Aryl‐α‐Diazo‐β‐Keto‐Amides with Functionalized Allyl Carbonates

Chen

Yang

et al. 2019

Adv Synth Catal

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A chemo-selective Rh(II)/Pd(0) dual catalysis that promotes one-pot synthesis of C3quaternary allylic oxindoles from N-aryl-a-diazo-bketoamides and functionalized allyl carbonates in good to excellent yields has been developed. The efficiency of this transformation relies on the choice of Rh(II)/Pd(0) dual catalysis strategy that enabled cascade intramolecular aryl CÀH insertion and allylic alkylation under mild conditions.

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Direct Alkenylation of 2‐Methylquinolines with Aldehydes through Synergistic Catalysis of 1,3‐Dimethylbarbituric Acid and HOAc

Liang

Wang

et al. 2019

Adv Synth Catal

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An efficient and practical direct alkenylation of 2-methylquinolines with aldehydes has been achieved through a novel synergistic organocatalysis. The HOAc-activated 2-methylquiolines undergo a Michael addition to 1,3-dimethylbarbituric acid-activated aldehydes, followed by a retro-Michael addition to release 1,3-dimethylbarbituric acid and the target products. The transformation produced various 2-alkenylquinolines with good to excellent yields and featured mild reaction conditions, atom-and step-economy, good functional group tolerance, and operational simplicity.

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Synergistic Cu/Pd Catalysis for Enantioselective Allylic Alkylation of Aldimine Esters: Access to α,α‐Disubstituted α‐Amino Acids

Cited by 36 publications

References 74 publications

Synergistic Dual Catalysis in Stereodivergent Synthesis

Synergistic Dual Catalysis in Stereodivergent Synthesis

Chemo‐selective Rh(II)/Pd(0) Dual Catalysis: Synthesis of All‐Carbon C3‐Quaternary Allylic Oxindoles from N‐Aryl‐α‐Diazo‐β‐Keto‐Amides with Functionalized Allyl Carbonates

Direct Alkenylation of 2‐Methylquinolines with Aldehydes through Synergistic Catalysis of 1,3‐Dimethylbarbituric Acid and HOAc

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