Magnesium Iodide Promoted Reactions of Nitrones with Cyclopropanes: A Synthesis of Tetrahydro-1,2-oxazines
- 1 November 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (24) , 8554-8557
- https://doi.org/10.1021/jo048768f
Abstract
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.Keywords
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