Modular amino acids‐based chiral ligands for copper‐catalyzed enantioselective conjugation addition of diethylzinc to cyclic enones

Gou, Shaohua; Judeh, Zaher M. A.

doi:10.1002/chir.20881

Chirality

2011

DOI: 10.1002/chir.20881

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Modular amino acids‐based chiral ligands for copper‐catalyzed enantioselective conjugation addition of diethylzinc to cyclic enones

Shaohua Gou

Zaher M. A. Judeh

Abstract: New amino acid-based modular chiral ligands were readily synthesized and used to catalyze the asymmetric conjugate addition of Et(2) Zn to various cyclic enones in the presence of a variety of copper sources. Moderately high ee of up to 72% were obtained using ligand (S)-1e under mild conditions.

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Cited by 3 publications

References 108 publications

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Modular amino acid amide chiral ligands for enantioselective addition of diethylzinc to aromatic aldehydes

Gou

Chang

et al. 2011

Applied Organom Chemis

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Enantioselective addition of diethylzinc to a series of aromatic aldehydes was developed using a modular amino acid amide chiral ligand (2S)-3-phenyl-N-((R)-1-phenyl-ethyl)-2-(tosylamino)propanamide without using titanium complex. The catalytic system employing 10 mol% of 1g was found to promote the addition of diethylzinc (ZnEt 2 ) to a wide range of aromatic aldehydes with electron-donating and electron-withdrawing substituents, giving up to 82% ee of the corresponding secondary alcohol under mild conditions.

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Modular amino acid amide chiral ligands for enantioselective addition of diethylzinc to aromatic aldehydes

Gou

Chang

et al. 2011

Applied Organom Chemis

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Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: computational rationale for enantioselectivity

et al. 2013

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A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%) and high enantioselectivity (up to 99%). The experimental results and DFT calculations suggest that para substituted aromatic aldehydes as substrate show higher ee in the product than their ortho/meta counterparts. The (1)H and (13)C NMR spectra study corroborated the calculated results. The chiral organocatalyst can be easily synthesized from optically pure phenylalanine in two simple steps with 90% overall yield.

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Functionalized BINOL-mono-PHOS for Multinuclear Cu-Catalysts in Asymmetric Conjugate Addition of Organozinc Reagents

et al. 2013

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Functionalization of BINOL-mono-PHOS achieved the Cu-catalyzed highly asymmetric conjugate addition of organozinc reagents to enones. The incorporation of a bulky hydroxy group at the 3′-position of BINOL-mono-PHOS dramatically improved the yield and enantioselectivity. The present novel BINOL-mono-PHOS ligands are effective in the Cu-catalyzed asymmetric conjugate addition of organozinc reagents in both acyclic enones and cyclohexenone.

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Modular amino acids‐based chiral ligands for copper‐catalyzed enantioselective conjugation addition of diethylzinc to cyclic enones

Cited by 3 publications

References 108 publications

Modular amino acid amide chiral ligands for enantioselective addition of diethylzinc to aromatic aldehydes

Modular amino acid amide chiral ligands for enantioselective addition of diethylzinc to aromatic aldehydes

Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: computational rationale for enantioselectivity

Functionalized BINOL-mono-PHOS for Multinuclear Cu-Catalysts in Asymmetric Conjugate Addition of Organozinc Reagents

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