Pd(II) complexes of monodentate deoxycholic acid derived binaphthyl diamido phosphites as chiral catalysts in the asymmetric Suzuki-Miyaura cross-coupling

Iannucci, Grazia; Passarelli, Vincenzo; Passera, Alessandro; Iuliano, Anna

doi:10.1016/j.tetasy.2017.09.012

Cited by 5 publications

(1 citation statement)

References 55 publications

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“…Providing optically active products from prochiral substrates in the presence of chiral catalysts gets great attention chiefly from economic view point, capability of production of favorable products and enantiomerically purity of them. [13] In this way different chiral catalysts have been introduced for the promotion of various organic reactions [14][15][16][17][18][19][20] which of them amino acids can be considered as the most tremendously important ones, which expedite asymmetric synthesis. Significant biological properties of amino acids led them be useful in nutrition, fertilizers and food technology.…”

Section: Introductionmentioning

confidence: 99%

First Asymmetric Synthesis of Passerini‐Type Condensation Products in Water Using Pregabalin: A Chiral Amino Acid for the Efficient Asymmetric Induction

Mousapour

Hassani²,

Shirini

2022

ChemistrySelect

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This article describes the use of Pregabalin as a commercially available chiral amino acid in the efficient synthesis of the Passerini‐type condensation products via two‐component condensation of aromatic aldehydes with cyclohexyl isocyanide. All reactions are accompanied with aerobic oxidation of aldehydes in water leading to chiral α‐acyloxycarboxamides with moderate to good enantioselectivities (up to 88 % ee) under green conditions such as nonmetal source. This is the first report of asymmetric synthesis of Passerini products in water.

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Section: Introductionmentioning

confidence: 99%

First Asymmetric Synthesis of Passerini‐Type Condensation Products in Water Using Pregabalin: A Chiral Amino Acid for the Efficient Asymmetric Induction

Mousapour

Hassani²,

Shirini

2022

ChemistrySelect

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Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols

Chuchelkin

Gavrilov

et al. 2021

Organometallics

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A large family of P,S-bidentate diamidophosphite ligands were readily synthesized from accessible hydroxyl-thioether compounds. One type of Pd(II) cationic allylic complex with these diamidophosphites fulfilling a P-monodentate function, and three types, where the ligands act as P,S-bridging ligands (coordination polymer and head-to-head and head-to-tail dimers), were obtained. In addition, neutral Pd(II) halide complexes were generated in situ as common intermediates for both groups of cationic dimers. The structures of the ligands and complexes were elucidated by means of 2D-NMR and were confirmed by powder X-ray diffraction, as well as by DFT calculations. Asymmetric inducers of this type exhibited up to 94% ee in the Pd-mediated allylic substitution of (E)-1,3-diphenylallyl acetate with various C- and N-nucleophiles. Ee values of up to 80% were obtained in the Pd-catalyzed allylic alkylation of cinnamyl acetate with β-ketoesters. In addition, up to 61% ee was achieved in the asymmetric amination of 2-(diethoxyphosphoryl)-1-phenylallyl acetate with aniline. The effects of the diamidophosphite and thioether moieties on the catalytic activity and enantioselectivity were investigated.

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Mechanistic insights into the tropo-inversion of the biphenyl moiety in chiral bis-amido phosphites and in their palladium(ii) complexes

et al. 2018

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Pd(II) complexes of monodentate deoxycholic acid derived binaphthyl diamido phosphites as chiral catalysts in the asymmetric Suzuki-Miyaura cross-coupling

Cited by 5 publications

References 55 publications

First Asymmetric Synthesis of Passerini‐Type Condensation Products in Water Using Pregabalin: A Chiral Amino Acid for the Efficient Asymmetric Induction

First Asymmetric Synthesis of Passerini‐Type Condensation Products in Water Using Pregabalin: A Chiral Amino Acid for the Efficient Asymmetric Induction

Formation of Allylpalladium Complexes and Asymmetric Allylation Involving Modular Bridging Diamidophosphite-Sulfides Based on 1,4-Thioether Alcohols

Mechanistic insights into the tropo-inversion of the biphenyl moiety in chiral bis-amido phosphites and in their palladium(ii) complexes

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