Sulfoxide-controlled SN2′ displacements between cuprates and vinyl and alkynyl epoxy sulfoxides |
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| Authors: | Roberto Ferná ndez de la Pradilla,Alma Viso,Sonia Castro,Jorge Ferná ndez,Pilar Manzano,Mariola Tortosa |
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| Affiliation: | Instituto de Química Orgánica, CSIC, Juan de la Cierva, 3, 28006 Madrid, Spain |
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| Abstract: | The SN2′ displacement of readily available vinyl epoxy sulfoxides with organocopper reagents takes place in good yields with high anti selectivity and a good degree of E/Z stereocontrol to produce enantiopure α-hydroxy vinyl sulfoxides. A second allylic displacement on the related mesyloxy vinyl sulfoxides allows for the asymmetric construction of two adjacent chiral centers. In addition, cuprate mediated SN2′ addition to alkynyl epoxy sulfoxides affords α-hydroxy allenyl sulfoxides in good yields. |
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| Keywords: | Sulfoxide Epoxide Cuprate Asymmetric SN2&prime Allenes |
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