SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. 45. REGIO- AND STEREOSELECTIVITY OF THE [2+3]-CYCLOADDITION OF E-BETA-NITROSTYRENE TO Z-C-PHENYL-N-ARYLNITRONES

Abstract

It is shown using spectroscopic methods that the [2+3]-cycloaddition of Z-C-phenyl-N-arylnitrones to E-β-nitrostyrene is regiospecific and leads to a mixture of the corresponding (3SR,4SR,5SR)- and (3SR,4RS,5RS)-2-aryl-4-nitro-3,5-diphenylisoxazolidines. The regioselectivity of the reaction is explained in terms of hard and soft acid and base theory.

Author: A.Baranski.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (6), pp 738-743

http://link.springer.com/article/10.1007/BF02297685