Lacôte Emmanuel, Delouvrié Bénédicte, Fensterbank Louis, Malacria Max
Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Université Pierre et Marie Curie, 4, place Jussieu, Tour 44-54, Case 229 F-75252 Paris Cedex 05 (France), Fax: (+33) 1-44-27-73-60.
Angew Chem Int Ed Engl. 1998 Aug 17;37(15):2116-2118. doi: 10.1002/(SICI)1521-3773(19980817)37:15<2116::AID-ANIE2116>3.0.CO;2-L.
Alkylidene-substituted cyclopentane derivatives are formed in high enantiomeric purity by the reaction shown below. A highly diastereoselective radical cyclization is followed by elimination of a β-sulfinyl radical. Interestingly, the addition of the Lewis acid methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) totally reverses the stereochemical outcome of the reaction. E=CO Me.
