1,3-Dipolar cycloaddition reaction of α,β-unsaturated esters and lactones with diazomethane

1,3-Dipolar cycloaddition of diazomethane to the α,β-unsaturated esters and lactones such as 2–4, 6–8, 10 and 13 occurs in a stereoselective manner affording conjugated Δ2-pyrazolines. E and Z isomers of D-mannitol lead to identical product which was cyclised to investigate the absolute stereochemis...

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Bibliographic Details
Published inTetrahedron Vol. 52; no. 12; pp. 4515 - 4526
Main Authors Baskaran, S., Vasu, J., Kodukulla, Ram Prasad.K., Trivedi, Girish K., Chandrasekhar, J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.03.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLO-ADDITION
DIAZOALKANES
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Summary:1,3-Dipolar cycloaddition of diazomethane to the α,β-unsaturated esters and lactones such as 2–4, 6–8, 10 and 13 occurs in a stereoselective manner affording conjugated Δ2-pyrazolines. E and Z isomers of D-mannitol lead to identical product which was cyclised to investigate the absolute stereochemistry of the product. the regiospecificities of all the reactions are consistent with FMO coefficients obtained through AM1 calculations. Dipolar cycloaddition of diazomethane with the following dipolarophiles was described.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00099-3