期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 69, 期 24, 页码 8554-8557出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo048768f
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Anhydrous magnesium iodide (MgI2) is shown to be an effective promoter of the homo 3+2 dipolar cycloaddition of nitrones with 1,1-cyclopropane diesters. In almost all cases the products tetrahydro-1,2-oxazines are formed in excellent yields. The reactions are highly diastereoselective for a cis relationship between the substitutents at the 3- and 6-positions on the tetrahydrooxazine ring. As an alternative to using a preformed nitrone, the reaction may be performed in a 3-component sense by combining an aldehyde, an hydroxylamine, and the cyclopropane in the presence of catalytic MgI2.
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