Manganese(III)-Mediated Radical Additions of Dimethyl Malonate to Olefins. The Chemoselective Synthesis of Diesters and Lactones

All articles of this category The radical addition of dimethyl malonate ( 1 ) to alkyl-substituted olefins 2a-d can be mediated by potassium permanganate and allows the chemoselective synthesis of saturated esters 4a-d . A high degree of stereoselectivity is observed with 1,5-cyclooctadiene ( 2d ) and trans -stilbene ( 2f ). In the presence of Mn(OAc) 3 the lactone 6f is obtained in diastereomerically pure form in 86% yield. radicals - manganese(III) - lactonization - chemoselectivity - potassium permanganate