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Enantioselective Cascade Reactions of Stable Sulfur Ylides and Nitroolefins through an Axial-to-Central Chirality Transfer Strategy

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posted on 20.01.2012 by Liang-Qiu Lu, Zhi-Hui Ming, Jing An, Chao Li, Jia-Rong Chen, Wen-Jing Xiao
An enantioselective [4 + 1] annulation/rearrangement cascade of stable sulfur ylides and nitroolefins has been developed through an efficient axial-to-central chirality transfer with the use of a chiral BINOL-derived sulfide as a reliable stereocontroller. It can provide pharmaceutically and synthetically important oxazolidinones in high stereoselectivities (up to 96:4 e.r. and >95:5 d.r.). Moreover, this strategy was also successfully applied to the asymmetric [4 + 1]/[3 + 2] cycloaddition cascade of sulfur ylides with alkene-tethered nitroolefins, and the corresponding enantioenriched fused heterocycles (up to 87:13 e.r. and >95:5 d.r.) were obtained in good to excellent yields (54–95% yields).