Stereoselective Synthesis of α‐Branched Amines by Nucleophilic Addition of Unstabilized Carbanions to Imines

Charette, André B.

doi:10.1002/9783527629541.ch1

Cited by 19 publications

(6 citation statements)

References 240 publications

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“…On the other hand, imines are useful intermediates in organic synthesis, acting as electrophilic reagents in many synthetic transformations, including addi-tions, condensations, and cycloadditions. Thus, the development of an easy synthetic protocol for the preparation of imines is highly desirable [16] [17] [18].…”

Section: Introductionmentioning

confidence: 99%

Efficient Solvent-Free Preparation of Imines, and Their Subsequent Oxidation with <i>m</i>-CPBA to Afford Oxaziridines

Álvarez-Santamaría¹,

Juaristi²,

Arroyo-Colín³

et al. 2019

GSC

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A simple one-pot procedure for the preparation of imines from the corresponding aldehydes and amines, and their subsequent oxidation reaction with m-CPBA to produce synthetically useful oxaziridines is reported. The method is applicable to imines derived from both aliphatic and aromatic aldehydes and diverse alkyl amines. Short reaction times, essentially quantitative yields, very mild reaction conditions, and easy purification are the main features of the procedure reported herein.

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Section: Introductionmentioning

confidence: 99%

Efficient Solvent-Free Preparation of Imines, and Their Subsequent Oxidation with <i>m</i>-CPBA to Afford Oxaziridines

Álvarez-Santamaría¹,

Juaristi²,

Arroyo-Colín³

et al. 2019

GSC

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“…Typical examples using N -arylketimines as a key precursor in various organic transformation are summarized in Scheme . In addition, ketimines are renowned building blocks for the preparation of α-chiral amines and ligands …”

Section: Introductionmentioning

confidence: 99%

Preparation of Ketimines from Aryldiazonium Salts, Arenes, and Nitriles via Intermolecular Arylation of N-Arylnitrilium Ions

et al. 2018

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A transition-metal-free approach for the preparation of N-arylketimines has been developed from the direct reaction of aryldiazonium salts, arenes, and nitriles in a one-pot fashion with the consecutive formation of N-C and C-C bonds. This approach proceeds via an in situ generation of N-arylnitrilium intermediate, which then undergoes intermolecular arylation. This three-component strategy offers a step- and atom-efficient way to N-arylketimines from easily accessible reagents under mild reaction conditions. The characterization of stereochemistry of ketimine was achieved by X-ray crystallographic structure and theoretical calculation. Operational simplicity, shorter reaction time, excellent functional group compatibility, and scalability are the key features of this report.

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“…This paper describes the rhodium(II)-catalyzed transformation of 5- and 4,5-substituted-1-STs 7 bearing allyl and propargylic ethers into stereodefined dihydrofuran-3-imines 9 (Scheme c). The imines themselves are valuable products, or they can be hydrolyzed under mild conditions to offer complementary access to 2,5- trans -disubstituted dihydrofuran-3-ones 5 . Furthermore, this reaction is shown to be effective for trisubstituted 1,2,3-triazoles 8 to give products 10 with controlled formation of a tetrasubstituted stereocenter.…”

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confidence: 99%

“…The N -tosylimine was unstable to purification by chromatography, but Rh 2 (OAc) 4 could be removed by filtration through Celite to give the product of denitrogenative rearrangement 9a . The N -tosylimine is a valuable functional group for further functionalization: the imine 9a could be hydrolyzed to the corresponding ketone 5a by stirring with wet basic alumina (Brockmann III) and also was an excellent substrate for reduction or nucleophilic attack which allowed facile generation of highly decorated tetrahydrofuran products 11a – 13a (Scheme ).…”

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confidence: 99%

Rhodium(II)-Catalyzed Stereocontrolled Synthesis of Dihydrofuran-3-imines from 1-Tosyl-1,2,3-triazoles

Boyer

2014

Org. Lett.

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Stereoselective Synthesis of α‐Branched Amines by Nucleophilic Addition of Unstabilized Carbanions to Imines

Cited by 19 publications

References 240 publications

Efficient Solvent-Free Preparation of Imines, and Their Subsequent Oxidation with <i>m</i>-CPBA to Afford Oxaziridines

Efficient Solvent-Free Preparation of Imines, and Their Subsequent Oxidation with <i>m</i>-CPBA to Afford Oxaziridines

Preparation of Ketimines from Aryldiazonium Salts, Arenes, and Nitriles via Intermolecular Arylation of N-Arylnitrilium Ions

Rhodium(II)-Catalyzed Stereocontrolled Synthesis of Dihydrofuran-3-imines from 1-Tosyl-1,2,3-triazoles

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Stereoselective Synthesis of α‐Branched Amines by Nucleophilic Addition of Unstabilized Carbanions to Imines

Cited by 19 publications

References 240 publications

Efficient Solvent-Free Preparation of Imines, and Their Subsequent Oxidation with &lt;i&gt;m&lt;/i&gt;-CPBA to Afford Oxaziridines

Efficient Solvent-Free Preparation of Imines, and Their Subsequent Oxidation with &lt;i&gt;m&lt;/i&gt;-CPBA to Afford Oxaziridines

Preparation of Ketimines from Aryldiazonium Salts, Arenes, and Nitriles via Intermolecular Arylation of N-Arylnitrilium Ions

Rhodium(II)-Catalyzed Stereocontrolled Synthesis of Dihydrofuran-3-imines from 1-Tosyl-1,2,3-triazoles

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Efficient Solvent-Free Preparation of Imines, and Their Subsequent Oxidation with <i>m</i>-CPBA to Afford Oxaziridines

Efficient Solvent-Free Preparation of Imines, and Their Subsequent Oxidation with <i>m</i>-CPBA to Afford Oxaziridines