Regioselective Reduction of 3-Methoxymaleimides: An Efficient Method for the Synthesis of Methyl 5-Hydroxytetramates.


3-Methoxymaleimide and various N-alkyl-3-methoxymaleimides, synthesized by base-promoted N-alkylation of 3-methoxymaleimide, were reduced using sodium borohydride with complete regioselectivity. The resultant Me 5-hydroxytetramates I (R = H, Me, Et, CH2CH:CH, Ph, CH2Ph, CH2C6H4-4-OMe) are useful intermediates in the synthesis of a variety of tetramate derivs.

Journal of Organic Chemistry