146334-96-5Relevant articles and documents
4,5-Dihydroisoxazole and 4,5-Dihydro-1,2,4-oxadiazole Derivatives from Cycloaddition Reactions of Nitrile Oxides to Alkyl N-(Diphenylmethylene)α,β-dehydroamino Acids
Balsamini, Cesarino,Spadoni, Gilberto,Bedini, Annalida,Tarzia, Giorgio,Lanfranchi, Maurizio,Pellinghelli, Maria Angela
, p. 1593 - 1598 (2007/10/02)
The alkyl N-(diphenylmethylene)-α,β-dehydroamino acids 1 have been submitted to 1,3-dipolar cycloadditions with nitrile oxides.The reactivity of these compounds depends on the type and on the stereochemistry of the β-substituents.With the unsubstituted terms 1a,b the reaction occurs on the C,C double bond, providing a good method for the synthesis of the 4,5-dihydroisoxazole derivatives 3a,b,c and for the gem-functionalized 4,5-dihydroisoxazoles amino carboxylic ester 5.The β-substituted compounds 1c,d,e, inert to 1,1-dimethylethylnitrile oxide, undergo the reaction to the N,C double bond, thus giving with 2a,b the 4,5-dihydro-1,2,4-oxadiazole derivatives 4.All the reactions occur with high site- and regioselectivity.