Tris(Pentafluorophenyl)Borane‐Driven Stereoselective <i>O</i>‐Glycosylation with Glycal Donors under Mild Condition

Mishra, Kunj B.; Kandasamy, Jeyakumar

doi:10.1002/ajoc.201900055

Cited by 11 publications

(1 citation statement)

References 31 publications

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“…Ferrier rearrangement is an allylic rearrangement of glycals . Classically, Ferrier rearrangement has been promoted by acid catalysts to form various glycosyl bonds, such as C–O, C–C, and C–S bonds (Scheme a), and chemical oxidants have also been reported as promoters (Scheme b). Most recently, Nagaki and coauthors reported that a flash electrochemical approach afforded efficient conversion using short-lived intermediates (Scheme c) .…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Carbon-Ferrier Rearrangement Using a Microflow Reactor and Machine Learning-Assisted Exploration of Suitable Conditions

Sato

Tachiwaki

Fujii

et al. 2023

Org. Process Res. Dev.

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The use of a flow reactor in electrolysis enables efficient and scalable synthesis, which is normally difficult to accomplish by batch reactors. We achieved electrochemical carbon-Ferrier rearrangement which proceeded with catalytic anodic oxidation, and this transformation could be performed using an electrochemical flow reactor. Additional numeric parameters derived from the flow reactor could be adjusted using Gaussian process regression (GPR), which is a machine learning method. GPR enables the construction of two models to estimate yields and productivity, and the reaction condition can be selected rationally.

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Section: Introductionmentioning

confidence: 99%

Electrochemical Carbon-Ferrier Rearrangement Using a Microflow Reactor and Machine Learning-Assisted Exploration of Suitable Conditions

Sato

Tachiwaki

Fujii

et al. 2023

Org. Process Res. Dev.

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Synthesis of Glycouronamides by Transamidation Approach at Room Temperature

et al. 2022

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Synthesis of various glycouronamides via transamidation reaction is reported under mild reaction conditions. Transamidation of N-nitroso uronamides with primary and secondary amines was successfully achieved in the presence of triethyl amine. On the other hand, N-Boc uronamides underwent transamidation smoothly with various primary amines in the presence of DBU. These reactions provided the desired glycouroamides in good to excellent yields at room temperature.

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o‐Cyanobenzoate: A Recyclable and Reusable Stereo‐directing Group for β‐O‐Glycosylation via Pd(0)‐catalyzed Ferrier Rearrangement

Thakur

Das

Molla

et al. 2021

Chemistry An Asian Journal

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Inner sphere Tsuji‐Trost reaction has found recent application for β‐selective Ferrier rearrangement of glycal substrates with alcohol nucleophiles. Herein, we report an efficient and stereoselective synthesis of 2,3‐dideoxy‐β‐O‐glycosides from C3‐(o‐cyanobenzoate) ester protected glycal donors via Ferrier rearrangement under Pd(0)‐catalyzed Tsuji‐Trost conditions. The synthesized donors indeed reacted with a variety of acceptors to afford the corresponding glycosides in good yields and excellent β‐stereoselectivity. The stereochemical outcome of the reactions has been found to be independent of the nature of protecting groups or conformational flexibility of the glycal donors. Furthermore, regeneration of ortho‐cyanobenzoic acid post rearrangement makes it a recyclable and reusable stereodirecting group. A preliminary mechanistic study demonstrates the importance of cyano‐group for the observed rearrangement and stereoselectivity. Incorporation of the directing group on the benzoate ester has altered the reactivity of the ester group as a leaving group for Tsuji‐Trost as well as Ferrier Rearrangement pathway.

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Tris(Pentafluorophenyl)Borane‐Driven Stereoselective O‐Glycosylation with Glycal Donors under Mild Condition

Cited by 11 publications

References 31 publications

Electrochemical Carbon-Ferrier Rearrangement Using a Microflow Reactor and Machine Learning-Assisted Exploration of Suitable Conditions

Electrochemical Carbon-Ferrier Rearrangement Using a Microflow Reactor and Machine Learning-Assisted Exploration of Suitable Conditions

Synthesis of Glycouronamides by Transamidation Approach at Room Temperature

o‐Cyanobenzoate: A Recyclable and Reusable Stereo‐directing Group for β‐O‐Glycosylation via Pd(0)‐catalyzed Ferrier Rearrangement

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