1,3-DIPOLAR CYCLOADDITION REACTION OF ALPHA,BETA-UNSATURATED ESTERS AND LACTONES WITH DIAZOMETHANE

Authors
BASKARAN S VASU J PRASAD R KODUKULLA K TRIVEDI GK CHANDRASEKHAR J
Citation
S. Baskaran et al., 1,3-DIPOLAR CYCLOADDITION REACTION OF ALPHA,BETA-UNSATURATED ESTERS AND LACTONES WITH DIAZOMETHANE, Tetrahedron, 52(12), 1996, pp. 4515-4526
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
12
Year of publication
1996
Pages
4515 - 4526
Database
ISI
SICI code
0040-4020(1996)52:12<4515:1CROAE>2.0.ZU;2-8
Abstract
1,3-Dipolar cycloaddition of diazomethane to the alpha,beta-unsaturate d esters and lactones such as 2-4, 6-8, 10 and 13 occurs in a stereose lective manner affording conjugated Delta(2)-pyrazolines. E and Z isom ers of D-mannitol lead to identical product which was cyclised to inve stigate the absolute stereochemistry of the product. The regiospecific ities of all the reactions are consistent with FMO coefficients obtain ed through AM1 calculations.