PPh3·HBr-DMSO Mediated Expedient Synthesis of g-Substituted b,g-Unsaturated a-Ketomethylthioesters and a-Bromo Enals: Application to the Synthesis of 2-Methylsulfanyl-3(2H)-furanones
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
PPh3·HBr-DMSO Mediated Expedient Synthesis of g-Substituted
b,g-Unsaturated a-Ketomethylthioesters and a-Bromo Enals: Application to the Synthesis of 2-Methylsulfanyl-3(2H)-furanones
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| Creator |
Mal, Kanchan
Sharma, Abhinandan Maulik, Prakas R. Das, Indrajit |
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| Subject |
Chemistry
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| Description |
An efficient chemoselective general procedure for the synthesis of g-substituted b,g-unsaturated a-ketomethylthioesters from a,b-unsaturated ketones has been
achieved through an unprecedented PPh3·HBr-DMSO mediated oxidative bromination and Kornblum oxidation sequence. The newly developed reagent system serves admirably for the synthesis of a-bromoenals from enals. Furthermore, AuCl3-catalyzed efficient access to 3(2H)-furanones from the above intermediates under extremely mild conditions are described.
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| Date |
2014
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/2016/1/CHEMISTRY%2DA_EUROPEAN_JOURNAL__Volume_20___Issue_3___Pages_662%2D667;2014(19).pdf
Mal, Kanchan and Sharma, Abhinandan and Maulik, Prakas R. and Das, Indrajit (2014) PPh3·HBr-DMSO Mediated Expedient Synthesis of g-Substituted b,g-Unsaturated a-Ketomethylthioesters and a-Bromo Enals: Application to the Synthesis of 2-Methylsulfanyl-3(2H)-furanones. Chemistry-A European journal, 20 (3). pp. 662-667. |
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| Relation |
http://dx.doi.org/ 10.1002/chem.201303755
http://www.eprints.iicb.res.in/2016/ |
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