Study of the Chemoselectivity of Grignard Reagent Addition to Substrates Containing Both Nitrile and Weinreb Amide Functionalities

Kommidi, Harikrishna; Rakshit, Ananya; Aidhen, Indrapal Singh

doi:10.1002/ejoc.201300622

Cited by 12 publications

(14 citation statements)

References 31 publications

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“…The reaction mixture was loaded directly and purified by flash column chromatography on silica gel (30% Et 2 O/n-Pentane) 13i; 80 mg, 30% yield; yellow solid; R f 0. 79 BrNO + [M + H] + requires 316.0332; found 316.0330. C 16 H 15 81 BrNO + [M + H] + requires 318.0312; found 318.0311.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles

et al. 2014

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The discovery of new methods for the synthesis of classes of potentially bioactive molecules remains an important goal for synthetic chemists. Vinylsulfonium salts have been used for the synthesis of a wide variety of small heterocyclic motifs; however, further developments to this important class of reagents has been focused on reaction with new substrates rather than development of new vinylsulfonium salts. We herein report the synthesis of a range of α-substituted vinylsulfonium tetraphenylborates (10 examples) in a 3 step procedure from commercially available styrenes. The important role of the tetraphenylborate counterion on the stability and accessibility of the vinylsulfonium salts is also detailed. The α-substituted vinylsulfonium tetraphenylborates gave good to excellent yields in the epoxyannulation of β-amino ketones (15 examples) and the cyclopropanation of allylic amines (4 examples). Hydrogenation of an epoxyannulation product proceeded with good diastereoselectivity.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles

et al. 2014

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“…Lepoittevin et al reported the preparation of 7-methoxy-4-arylcoumarin 50 from 2-hydroxybenzophenone 48 by the Wittig reaction in the synthesis of ( R )- and ( S )-4-methoxyalbergione [ 78 ]. In 2013, Aidhen et al have also reported the synthesis of 4-arylcoumarin 51 as an intermediate for MK-0633 [ 79 ] under conditions similar to those reported by Lepoittevin ( Scheme 10 A). These one-pot synthesis for the target molecules are proceeded under reflux conditions in toluene solvent.…”

Section: Synthetic Routes Toward Central 2-pyrone Of 4-arylcoumarimentioning

confidence: 77%

Recent Advances in Synthesis of 4-Arylcoumarins

et al. 2018

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4-Arylcoumarins (4-aryl-2H-1-benzopyran-2-one), also known as neoflavones, comprise a minor subclass of naturally occurring flavonoids. Because of their broad-spectrum biological activities, arylcoumarins have been attracting the attention of the organic and medicinal chemistry communities, and are considered as an important privileged scaffold. Since the development of Pechmann condensation, a classical acid-catalyzed condensation between phenol and β-keto-carboxylic acid, several versatile and efficient synthetic approaches for 4-arylcoumarins have been reported. This review summarizes recent advances in the synthesis of the 4-arylcoumarin scaffold by classifying them based on the final bond-formation type. In particular, synthetic methods executed under mild and highly efficient conditions, such as solvent-free reactions and transition metal catalysis, are highlighted.

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“…Structures of known compounds, 1a , 1b , 1c , 1d , 1e , 1f , 1g , 1h , 1i , 1k , 1l , 2a , 2b , 2c , 2d , 2e , 2f , 2g , 2h , 2j , 2k , 2l , 2m , 3a , 3b , 3c , 3d , 3e , 3f , 3h , 3i , and 3l ,were confirmed by NMR spectral comparison with literature data.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric Synthesis of Enantioenriched 6-Hydroxyl Butyrolactams Promoted by N-Heterocyclic Carbene

Zhu

et al. 2019

J. Org. Chem.

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Study of the Chemoselectivity of Grignard Reagent Addition to Substrates Containing Both Nitrile and Weinreb Amide Functionalities

Cited by 12 publications

References 31 publications

Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles

Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles

Recent Advances in Synthesis of 4-Arylcoumarins

Asymmetric Synthesis of Enantioenriched 6-Hydroxyl Butyrolactams Promoted by N-Heterocyclic Carbene

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