Selective Reductions of Cyclic 1, 3??Diesters by Using SmI2 and H2O

…, S De Grazia, H Matsubara, M Helliwell…

Index: Collins, Karl D.; Oliveira, Juliana M.; Guazzelli, Giuditta; Sautier, Brice; De Grazia, Sara; Matsubara, Hiroshi; Helliwell, Madeleine; Procter, David J. Chemistry - A European Journal, 2010 , vol. 16, # 33 p. 10240 - 10249

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Citation Number: 38

Abstract

Abstract SmI 2/H 2 O reduces cyclic 1, 3-diesters to 3-hydroxyacids with no over reduction. Furthermore, the reagent system is selective for cyclic 1, 3-diesters over acyclic 1, 3-diesters, and esters. Radicals formed by one-electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes. The ketal unit and the reaction temperature have a marked impact on the diastereoselectivity of the cyclizations. ...

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