Palladium-Mediated Intramolecular Aryl Amination on Furanose Derivatives: An Expedient Approach to the Synthesis of Chiral Benzoxazocine Derivatives and Tricyclic Nucleosides
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
Palladium-Mediated Intramolecular Aryl Amination on Furanose Derivatives: An Expedient Approach to the Synthesis of Chiral Benzoxazocine Derivatives and Tricyclic
Nucleosides
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| Creator |
Neogi, Arpita
Majhi, Tirtha Pada Mukhopadhyay, Ranjan Chattopadhyay, Partha |
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| Subject |
Chemistry
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| Description |
Pd-catalyzed intramolecular arylamination on sugar derivatives has been accomplished by using bulky biaryl phosphine ligands. An application of this methodology on a variety of D-glucose-derived substrates, 2a-f, led to the synthesis of highly functionalized cis-fused tricyclic oxazocines, 3a-e. The products could subsequently be transformed to the optically active benzoxazocine derivative 4 and tricyclic nucleoside 6. This is the first example of the synthesis of eight-membered rings via intramolecular cycloamination of furanose derivatives, which provides a very useful method for the catalytic synthesis of medium-ring heterocycles
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| Date |
2006
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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/400/1/JOURNAL_OF_ORGANIC_CHEMISTRY%2C__71(_8)%2C_3291%2D3294[102].pdf
Neogi, Arpita and Majhi, Tirtha Pada and Mukhopadhyay, Ranjan and Chattopadhyay, Partha (2006) Palladium-Mediated Intramolecular Aryl Amination on Furanose Derivatives: An Expedient Approach to the Synthesis of Chiral Benzoxazocine Derivatives and Tricyclic Nucleosides. The Journal of Organic Chemistry, 71. pp. 3291-3294. |
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| Relation |
http://dx.doi.org/10.1021/jo052420i CCC: $33.50
http://www.eprints.iicb.res.in/400/ |
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