Recent Advances in the Construction of Quaternary Stereocenters via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

Yu, Xiaoyan; Zhang, Ting; Liu, Jitian; Li, Xiaoxun

doi:10.1055/a-1533-3085

Cited by 13 publications

(2 citation statements)

References 70 publications

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“…It was envisioned that the enantioselective insertion of Rh(II)-carbenoid into C-H bond, followed by Pd(0)-catalyzed allylic alkylation of the resulting lactam would be an efficient and environmentally benign strategy to construct quaternary stereogenic centers. 14 Indeed, we have demonstrated that an asymmetric cooperative dual Rh(II)/Pd(0) relay catalysis could provide -quaternary allylated chiral -lactams with high yields and excellent stereoselectivities. 6d Thus, the reaction of 10a with allyl Boc carbonate 11a in the presence of Rh2[(S)-tert-PTTL]4 and Pd(dba)2/rac-BINAP catalysts afforded 12aa with excellent yield and stereoselectivities (99%, dr=91:1, 96% ee, Scheme 8a).…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Cooperative Rh(II)/Pd(0) Dual Catalysis for the Synthesis of Carbo- and Heterocyclic Compounds

Lee

Choi

et al. 2021

Synthesis

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Dual transition-metal catalysis has been introduced as a robust tool to synthesize a diverse range of organic compounds which are not able to be accessed by traditional single metal catalysis. In this context, we have recently developed the cooperative Rh(II)/Pd(0) dual catalytic systems, which have been utilized for the preparation of carbo- and heterocyclic compounds through the reaction between Rh(II)-carbenoid and π-allyl Pd(II)-complex intermediates in either synergistic or tandem relay catalysis. In synergistic Rh(II)/Pd(0) dual catalysis, the two reactive intermediates are generated simultaneously, which then undergo formal [6+3] dipolar cycloaddition to afford medium-sized N,O-heterocyclic compounds. On the other hand, tandem relay dual catalysis can be enabled through judicious choice of reaction parameters, which proceed through the insertion of Rh(II)-carbenoid into O–H or C–H bonds, followed by Pd(0)-catalyzed allylation to provide allylated benzofused cyclic compounds or chiral β-lactam derivatives.

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Section: Accepted Manuscriptmentioning

confidence: 99%

Cooperative Rh(II)/Pd(0) Dual Catalysis for the Synthesis of Carbo- and Heterocyclic Compounds

Lee

Choi

et al. 2021

Synthesis

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“…As a result, considerable effort has been devoted to the development of efficient approaches for the enantioselective construction of quaternary carbon stereocenters. 2,3 Compared to the well-studied cyclic quaternary carbon stereocenters, 2 the strategies for the enantioselective construction of acyclic quaternary carbon stereocenters are relatively few, probably due to additional problems such as the reduced rigidity of certain substrates leading to lower levels of selectivity. 3 In this domain, the use of stereodefined trisubstituted alkenes as substrates for enantioselective conjugate addition, 4 allylic substitution 5 or nucleophilic allylation reactions 6 is a predominant method for constructing chiral acyclic quaternary carbon stereocenters.…”

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confidence: 99%

Palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates: access to chiral acyclic quaternary carbon stereocenters

Bao,

Sun,

Zhang

et al. 2023

Org. Chem. Front.

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Advancements in Asymmetric Catalytic Approaches Involving Benzoxazinone Derivatives

et al. 2023

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Chiral aza‐heterocycles, as a sort of key frameworks of natural products et al, are deeply concerned by synthetic chemists. In recent years, catalytic asymmetric reactions of several types of zwitterionic intermediates, originating form benzoxazinone derivatives, have become a popular and efficient approach to obtain chiral aza‐heterocycles. Given that, this review attempts to summarize recent development in the field of catalytic asymmetric reactions of benzoxazinone derivatives as a powerful dipole precursors for the construction of aza‐heterocycles. In the past years, various benzoxazinone derivatives and their catalytic asymmetric reactions have been developed. Herein, this review is organized by the types of benzoxazinone derivatives and their catalytic asymmetric reactions to display their important synthetic potentials and values.

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Recent Advances in the Construction of Quaternary Stereocenters via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

Cited by 13 publications

References 70 publications

Cooperative Rh(II)/Pd(0) Dual Catalysis for the Synthesis of Carbo- and Heterocyclic Compounds

Cooperative Rh(II)/Pd(0) Dual Catalysis for the Synthesis of Carbo- and Heterocyclic Compounds

Palladium-catalyzed enantioselective decarboxylative allylic alkylation of α-benzyl cyanoacetates: access to chiral acyclic quaternary carbon stereocenters

Advancements in Asymmetric Catalytic Approaches Involving Benzoxazinone Derivatives

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