jo202324f_si_001.cif (14.5 kB)
Enantioselective Cascade Reactions of Stable Sulfur Ylides and Nitroolefins through an Axial-to-Central Chirality Transfer Strategy
dataset
posted on 2012-01-20, 00:00 authored by Liang-Qiu Lu, Zhi-Hui Ming, Jing An, Chao Li, Jia-Rong Chen, Wen-Jing XiaoAn 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).
History
Usage metrics
Categories
Keywords
cycloadditionTransfersulfideenantioenrichedenantioselectiveStable Sulfur YlidestransfersyntheticallyannulationchiralitystereoselectivitieEnantioselective Cascade ReactionsstrategystereocontrollerheterocycleChiralitypharmaceuticallyStrategyAnNitroolefinsulfur ylideschiralyieldcascadee.roxazolidinoned.rnitroolefin
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC