Highly enantio- and diastereoselective reactions of γ-substituted butenolides through direct vinylogous conjugate additions
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
Chemical Science Program
Homogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Sciences and Engineering (PSE) Division
Permanent link to this recordhttp://hdl.handle.net/10754/562320
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AbstractThe strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
SponsorsThis work was supported by the NSFC (21072044) and the Excellent Youth Foundation of Henan Scientific Committee (114100510003) to Z.J., and by KAUST to K.-W.H.
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