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Synthesis of Chiral 10, 11 and 12-Membered Nitrogen and Oxygen Heterocycles by Intramolecular Nitrile Oxide Cycloaddition of Tethered N- and O-Allyl Carbohydrate Derivatives

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Title Synthesis of Chiral 10, 11 and 12-Membered Nitrogen and Oxygen Heterocycles by Intramolecular Nitrile Oxide Cycloaddition of Tethered N- and O-Allyl Carbohydrate Derivatives
 
Creator Majumdar, Swapan
Mukhopadhyay, Ranjan
Bhattacharjya, Anup
 
Subject Chemistry
 
Description ÐChiral 10 to 12-membered nitrogen and oxygen heterocycles fused to isoxazoline rings have been prepared in a highly
regioselective and stereoselective manner by intramolecular nitrile oxide cycloaddition of tethered N- and O-allyl carbohydrate derivatives.
The use of a ±Y±Ar-CH2 tether containing a 1,2-disubstituted aromatic ring between the heteroatom attached to the nitrile oxide-bearing
carbohydrate scaffold, and the allyl group, facilitates the formation of the medium-sized rings. The cycloaddition afforded bridged isoxazolines
in the cases of O-tethered allyl carbohydrate derivatives, whereas a fused isoxazoline resulted when a N(Ts)-tethered allyl derivative
was used.
 
Publisher Elsevier
 
Date 2000
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/885/1/TETRAHEDRON__56(45)_8945%2D8951;2000[8].pdf
Majumdar, Swapan and Mukhopadhyay, Ranjan and Bhattacharjya, Anup (2000) Synthesis of Chiral 10, 11 and 12-Membered Nitrogen and Oxygen Heterocycles by Intramolecular Nitrile Oxide Cycloaddition of Tethered N- and O-Allyl Carbohydrate Derivatives. Tetrahedron, 56 (45). pp. 8945-8951.
 
Relation http://dx.doi.org/10.1016/S0040-4020(00)00844-9
http://www.eprints.iicb.res.in/885/