Two-Step Kinetic Resolution of Racemic Secondary Benzylic Alcohols Using the Combination of Enantioselective Silylation and Acylation: One-Pot Procedure Catalyzed by Chiral Guanidine

Miyazaki, Kouji; Nakata, Kenya

doi:10.1021/acs.joc.2c01129

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Cited by 4 publications

References 53 publications

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Synthesis of Organosilanes, Silyl Ethers, and Silanols

Liu,

Shi,

Zhang

et al. 2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Synthesis of Organosilanes, Silyl Ethers, and Silanols

Liu,

Shi,

Zhang

et al. 2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Acylative and Silylative Dynamic Kinetic Resolutions of 6-Hydroxy-2H-pyran-3(6H)-one Catalyzed by Chiral Guanidines

Nakata,

Miyazaki

2023

Synlett

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Chiral guanidine-catalyzed acylative and silylative dynamic kinetic resolutions of 6-hydroxy-2H-pyran-3(6H)-one were achieved. We succeeded in developing a non-enzymatic acylative dynamic kinetic resolution of 6-hydroxy-2H-pyran-3(6H)-one with high enantioselectivity, which could be improved by recrystallization. In contrast, the non-enzymatic silylative dynamic kinetic resolution of 6-hydroxy-2H-pyran-3(6H)-one was accomplished with a moderate selectivity for the first time.

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Enantioselective Silylative Desymmetrization of meso-Indane-1,3-diols Catalyzed by Chiral Guanidines

Nakata,

Ui,

Iwakura

et al. 2024

Synlett

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Chiral guanidine-catalyzed desymmetrization of meso-indan-1,3-diols was achieved via enantioselective silylation by using chlorosilanes in good yields with high selectivity. The combination of chlorosilanes and catalysts was determined by the substituents at the C-2 position on the substrate. It was found that the fused phenyl ring on the substrate was essential for achieving high selectivity. The proposed method was found to be applicable to several types of substrates under optimized reaction conditions. Double silylative kinetic resolution with additive Horeau amplification was observed to establish high selectivity.

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Two-Step Kinetic Resolution of Racemic Secondary Benzylic Alcohols Using the Combination of Enantioselective Silylation and Acylation: One-Pot Procedure Catalyzed by Chiral Guanidine

Abstract: A novel two-step kinetic resolution of racemic secondary benzylic alcohols with practical enantiomeric ratios was achieved. The reactions were carried out via a one-pot operation by combining enantioselective silylation and acylation mediated by the same chiral guanidine catalyst.

Cited by 4 publications

References 53 publications

Synthesis of Organosilanes, Silyl Ethers, and Silanols

Synthesis of Organosilanes, Silyl Ethers, and Silanols

Acylative and Silylative Dynamic Kinetic Resolutions of 6-Hydroxy-2H-pyran-3(6H)-one Catalyzed by Chiral Guanidines

Enantioselective Silylative Desymmetrization of meso-Indane-1,3-diols Catalyzed by Chiral Guanidines

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