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Synlett 1996; 1996(5): 468-470
DOI: 10.1055/s-1996-5451
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Manganese(III)-Mediated Radical Additions of Dimethyl Malonate to Olefins. The Chemoselective Synthesis of Diesters and Lactones

Torsten Linker* , Berthold Kersten, Ursula Linker, Karl Peters, Eva-Maria Peters, Hans Georg von Schnering
  • *Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany
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Publication Date:
31 December 2000 (online)

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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