Palladium‐Catalyzed Decarboxylative Asymmetric Allylic Alkylation: Development, Mechanistic Understanding and Recent Advances

James, Jinju; Jackson, Mark; Guiry, Patrick J.

doi:10.1002/adsc.201801575

Cited by 88 publications

(35 citation statements)

References 154 publications

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“… 7 , 8 The generally accepted mechanism of the DAAA involves the coordination of the Pd(0) complex to the allyl moiety leading to oxidative addition, followed by the loss of CO 2 to generate the Pd enolate 18-Y , which then attacks the intermediate allyl group to form the enantioenriched product 19 and regenerate the Pd(0) catalyst. 9 …”

Section: Mono(oxazoline) Ligandsmentioning

confidence: 99%

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

et al. 2021

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The chiral oxazoline motif is present in many ligands that have been extensively applied in a series of important metal-catalyzed enantioselective reactions. This Review aims to provide a comprehensive overview of the most significant applications of oxazoline-containing ligands reported in the literature starting from 2009 until the end of 2018. The ligands are classified not by the reaction to which their metal complexes have been applied but by the nature of the denticity, chirality, and donor atoms involved. As a result, the continued development of ligand architectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof can be more easily monitored by the reader. In addition, the key transition states of selected asymmetric transformations will be given to illustrate the features that give rise to high levels of asymmetric induction. As a further aid to the reader, we summarize the majority of schemes with representative examples that highlight the variation in % yields and % ee s for carefully selected substrates. This Review should be of particular interest to the experts in the field but also serve as a useful starting point to new researchers in this area. It is hoped that this Review will stimulate both the development/design of new ligands and their applications in novel metal-catalyzed asymmetric transformations.

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Section: Mono(oxazoline) Ligandsmentioning

confidence: 99%

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

et al. 2021

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“…A comprehensive overview over mechanistic studies on decarboxylative allylic alkylations was given by Guiry et al . in a recent review article from 2019 [63] …”

Section: Decarboxylative Allylic Alkylationsmentioning

confidence: 99%

“…A comprehensive overview over mechanistic studies on decarboxylative allylic alkylations was given by Guiry et al in a recent review article from 2019. [63] In 2005, Trost and Xu reported on the use of ligand L1c in the decarboxylative allylation of cyclic ketones. [64] In this reaction, ligand L1c seemed to be superior to the previously applied L1a, resulting in enantiomeric excesses ranging from 76 % to more than 99 % (Scheme 39).…”

Section: Decarboxylative Allylic Alkylations Of Cyclic Ketonesmentioning

confidence: 99%

The Allylic Alkylation of Ketone Enolates

Junk

Kazmaier

2020

ChemistryOpen

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The palladium‐catalyzed allylic alkylation of non‐stabilized ketone enolates was thought for a long time to be not as efficient as the analogous reactions of stabilized enolates, e. g. of malonates and β‐ketoesters. The field has experienced a rapid development during the last two decades, with a range of new, highly efficient protocols evolved. In this review, the early developments as well as current methods and applications of palladium‐catalyzed ketone enolate allylations will be discussed.

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“…Recently, much progress has been made in this area, especially with respect to efficient new protocols for the assembly of complex all-carbon quaternary stereocenters. [23][24][25][26] This review will summarize examples of the direct construction of quaternary stereocenters by means of palladium-catalyzed decarboxylative asymmetric allylic alkylation since 2018. Selected recent total synthesis of complex natural products involving DAAA as the key step are also presented.…”

Section: Introductionmentioning

confidence: 99%

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

Zhang

Liu

et al. 2021

Synthesis

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Palladium catalyzed decarboxylative asymmetric allylic alkylation (DAAA) provides an efficient and powerful strategy to construct quaternary stereocenters which are widely present in biologically active natural products and approved drugs. In this short review, we summarize recent developments (since 2018) in the facile synthesis of quaternary stereocenters via DAAA methods. Several representative examples by using DAAA strategy for total synthesis of complex natural products further demonstrate its synthetic potential in the realm of organic and medicinal chemistry

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Palladium‐Catalyzed Decarboxylative Asymmetric Allylic Alkylation: Development, Mechanistic Understanding and Recent Advances

Cited by 88 publications

References 154 publications

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

The Allylic Alkylation of Ketone Enolates

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

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