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Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β‑Unsaturated Oxazolidin-2-one Derivatives
journal contribution
posted on 2017-11-18, 20:14 authored by Samuel Lauzon, Hoda Keipour, Vincent Gandon, Thierry OllevierA highly enantioselective
FeII-catalyzed thia-Michael
addition to α,β‑unsaturated carbonyl derivatives
was developed. The scope of the reaction was demonstrated with a selection
of aromatic, heterocyclic and aliphatic thiols, and various Michael
acceptors. The corresponding β-thioethers were obtained in good
to excellent yields (up to 98%) and moderate to excellent enantioselectivities
(up to 96:4 er). Unusual hepta-coordination of the metal and chelation
to α,β-unsaturated oxazolidin-2-one derivatives allowed
the construction of a coherent model rationalizing the enantioselective
event. DFT calculations support the proposed model for observed stereoselectivities.
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Asymmetric Fe IIheterocyclicoxazolidin -2-one derivativesOxazolidinCatalyzed Thia-Michael Addition Reactionthia-Michael additionDerivativeMichael acceptorsUnusual hepta-coordinationstereoselectivitieenantioselective eventenantioselectivitieconstructionscopealiphatic thiolsβ- thioetherscarbonyl derivativesyieldchelationenantioselective Fe IImodelDFT calculations supportUnsaturated
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