Enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated ketones catalyzed by oxazaborolidines

Qian, Jinyi; Zhao, Hengyuan; Gao, Qi; Chen, Lirong; Shi, Yinrui; Li, Jiuling; Guo, Yafei; Fan, Baomin

doi:10.1039/d3qo01178j

Cited by 4 publications

(1 citation statement)

References 54 publications

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“…The proline-derived oxazaborolidines have been extensively studied for their applications in enantioselective reduction and cycloaddition reactions . Recently, we reported a highly efficient metal-free catalytic system for the enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated thioesters and ketones (Scheme C) . Interestingly, the commercially available classical oxazaborolidines (CBS) were found to possess this catalytic ability despite being widely used for over 30 years.…”

Section: Introductionmentioning

confidence: 99%

Metal-Free Enantioselective 1,4-Addition of Diarylphosphine Oxides to α,β-Unsaturated Carboxylic Esters

Lu,

Xiao,

Que

et al. 2024

J. Org. Chem.

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The catalytic asymmetric conjugate addition of phosphorus nucleophiles to unsaturated compounds, catalyzed by metallic or nonmetallic catalysts, has been extensively developed. However, the enantioselective transformations involving α,β-unsaturated carboxylic esters for constructing chiral c-p bonds have been rarely reported, particularly in metal-free processes. In this study, we present a novel metal-free methodology for enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated carboxylic esters using classical chiral oxazaborolidine catalysts. Remarkably high yields and enantioselectivities were obtained for most of the products. Furthermore, these valuable chiral phosphorus esters serve as crucial intermediates that can be transformed into various derivatives including amides, acids, and alcohols in a single step.

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Section: Introductionmentioning

confidence: 99%

Metal-Free Enantioselective 1,4-Addition of Diarylphosphine Oxides to α,β-Unsaturated Carboxylic Esters

Lu,

Xiao,

Que

et al. 2024

J. Org. Chem.

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Asymmetric 1,4‐Addition of Diarylphosphine Oxides to α, β‐Unsaturated 2‐Acyl Imidazoles

Chen,

Wang,

Nong

et al. 2024

Chemistry A European J

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Here we introduce a metal‐free, catalytic and enantioselective strategy from α,β‐unsaturated 2‐acyl imidazoles to the chiral phosphorous 2‐acyl imidazoles. Interestingly, this methodology was catalyzed by the classical and commercial oxazaborolidine under mild conditions. This strategy features a wide range of substrates scope with good yields and excellent enantioselectivities. The possible mechanism further suggests the key of this reaction through the cleavage of diarylphosphine oxides using Frustrated Lewis Pairs theory.

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Oxazaborolidine catalyzed asymmetric 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles

Qian,

Shao,

Gao

et al. 2024

Tetrahedron

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Enantioselective 1,4-addition of diarylphosphine oxides to α,β-unsaturated ketones catalyzed by oxazaborolidines

Abstract: A new application of oxazaborolidines in enantioselective phospha-Michael addition to α,β-unsaturated ketones under mild reaction conditions was developed and the possible mechanism is described.

Cited by 4 publications

References 54 publications

Metal-Free Enantioselective 1,4-Addition of Diarylphosphine Oxides to α,β-Unsaturated Carboxylic Esters

Metal-Free Enantioselective 1,4-Addition of Diarylphosphine Oxides to α,β-Unsaturated Carboxylic Esters

Asymmetric 1,4‐Addition of Diarylphosphine Oxides to α, β‐Unsaturated 2‐Acyl Imidazoles

Oxazaborolidine catalyzed asymmetric 1,4-addition of diarylphosphine oxides to α,β-unsaturated N-acylindoles and N-acylpyrroles

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