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
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| 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/ |
|