Selective Addition of Carbamoylsilane to Vicinal Diketones: Highly Efficient Synthesis of β-Keto-α-hydroxyamides

Cao, Ping; Wen, Xueping; Chen, Jianxin

doi:10.1055/s-0036-1588346

Synlett

2016

DOI: 10.1055/s-0036-1588346

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Selective Addition of Carbamoylsilane to Vicinal Diketones: Highly Efficient Synthesis of β-Keto-α-hydroxyamides

Ping Cao

Xueping Wen

Jianxin Chen

Abstract: The selective addition of carbamoylsilane to vicinal diketones in toluene solvent at 110 °C affords β-keto-α-siloxyamide derivatives in good yields (54-99%). The steric hindrance is an important factor in the addition reaction.

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E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^–

Tian¹,

Sun²,

Wang³

et al. 2023

Chinese Journal of Organic Chemistry

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The difunctionalization of alkenes and alkynes is a simple and powerful strategy for the synthesis of various organic compounds and has been used to synthesize various important natural products, drug molecules and fine chemical products. The different effects of halo anions, substrates, solvents, temperature and reaction time to the stereospecific and reactivities of 1,1-carboborations of alkynes and B(C6F5)s were studied, meanwhile the corresponding catalytic mechanisum has been expoled. A convenient large-scale preparation method for the stereoselective (E)-1,1-carboboration products has been developed. The catalytic reactivities of ring-opening polymerization of cyclohexene oxide (CHO) have also been explored with different stereo-carboboranes isolated from 1,1-carboboration reaction, and it is noted that the stereospecificity E-or Z-has shown ambiguously different activities. To develop a stereo-specific approach in the synthesis of vinylboranes will not only be very important for the difunctionalization of alkenes and alkynes, but also for the novel stereospecificity organoborons.

show abstract

E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^–

Tian¹,

Sun²,

Wang³

et al. 2023

Chinese Journal of Organic Chemistry

View full text Add to dashboard Cite

show abstract

Synthesis of β-Nitroamide Derivatives Based on Carbamoylsilane

Li¹,

Han²,

Liu³

et al. 2022

Chinese Journal of Organic Chemistry

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Selective Addition of Carbamoylsilane to Vicinal Diketones: Highly Efficient Synthesis of β-Keto-α-hydroxyamides

Abstract: The selective addition of carbamoylsilane to vicinal diketones in toluene solvent at 110 °C affords β-keto-α-siloxyamide derivatives in good yields (54-99%). The steric hindrance is an important factor in the addition reaction.

Cited by 2 publications

References 4 publications

E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^–

E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^–

Synthesis of β-Nitroamide Derivatives Based on Carbamoylsilane

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Selective Addition of Carbamoylsilane to Vicinal Diketones: Highly Efficient Synthesis of β-Keto-α-hydroxyamides

Abstract: The selective addition of carbamoylsilane to vicinal diketones in toluene solvent at 110 °C affords β-keto-α-siloxyamide derivatives in good yields (54-99%). The steric hindrance is an important factor in the addition reaction.

Cited by 2 publications

References 4 publications

E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C6F5)3]–

E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C6F5)3]–

Synthesis of β-Nitroamide Derivatives Based on Carbamoylsilane

Contact Info

Product

Resources

About

E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^–

E-Stereospecific 1,1-Carboboration of Terminal Arylalkynes with [IB(C₆F₅)₃]^–