Dimethyl [(2R,3R,5S)‐5‐phenylmorpholine‐2,3‐diyl]diacetate as a Designer Substrate in the Syntheses of Important Heterocyclic Scaffolds

Pandey, Ganesh; Gaikwad, Amrut L.; Gadre, Smita R.

doi:10.1002/ajoc.201200033

Cited by 4 publications

(1 citation statement)

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“…LiBF 4 was also required and acts as a Lewis acid to activate the enone. Subsequently, the activated enone was reduced to the key radical anion intermediate 480 by Ru(bpy) 3 + . − As a limitation of this protocol, aliphatic enones and enoates did not cyclize. Their more negative reduction potential seemed to prevent reduction to the radical anions.…”

Section: Pet Catalysis–photoredox Catalysismentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

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Section: Pet Catalysis–photoredox Catalysismentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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Copper‐Catalyzed β‐Iodovinylation of Carbamates: Expedient Access to Highly Functionalized Vinyl‐Carbamates

2018

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A general and efficient method for the synthesis of β‐iodovinyl carbamates via copper‐catalyzed β‐iodovinylation of acyclic carbamates is described. This method uses readily available (E)‐1,2‐vinyl diiodides and regioselectively affords the corresponding β‐iodovinyl carbamates in good yields with complete stereocontrol of the alkene. Further functionalization of these versatile products leads to a wide diversity of β‐functionalized vinyl‐carbamates in good to excellent yields.

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Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

Phae-nok¹,

Kuhakarn²,

Leowanawat³

et al. 2022

Synlett

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Decarboxylative transformations of paraconic acids, a class of γ-butyrolactones containing a carboxylic acid group at the β position as their characteristic functionality, using a combination of AgNO3/K2S2O8 was investigated. The dual function of AgNO3 as an initiator for decarboxylation process and a nitrogen dioxide radical source that reacts with aliphatic carboxylic substrates of this study was reported for the first time. Starting from paraconic acids, β-nitro- and β-hydroxy γ-butyrolactones were obtained in good combined yields (41-85% yields) with moderate selectivity in one-pot operation. The reactions completed within acceptable reaction time (2 h) under mild reaction conditions that γ-butyrolactone core could be tolerated. The present study represents the direct and site-specific entry to β-nitro- and β-hydroxy γ-butyrolactones which are important precursors in organic transformations.

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Dimethyl [(2R,3R,5S)‐5‐phenylmorpholine‐2,3‐diyl]diacetate as a Designer Substrate in the Syntheses of Important Heterocyclic Scaffolds

Cited by 4 publications

References 85 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Copper‐Catalyzed β‐Iodovinylation of Carbamates: Expedient Access to Highly Functionalized Vinyl‐Carbamates

Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

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Dimethyl [(2R,3R,5S)‐5‐phenylmorpholine‐2,3‐diyl]diacetate as a Designer Substrate in the Syntheses of Important Heterocyclic Scaffolds

Cited by 4 publications

References 85 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Copper‐Catalyzed β‐Iodovinylation of Carbamates: Expedient Access to Highly Functionalized Vinyl‐Carbamates

Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

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Product

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About

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions