Asymmetric FeII-Catalyzed Thia-Michael
Addition Reaction to α,β‑Unsaturated Oxazolidin-2-one
Derivatives
Posted on 2017-11-18 - 20:14
A 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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Lauzon, Samuel; Keipour, Hoda; Gandon, Vincent; Ollevier, Thierry (2017). Asymmetric FeII-Catalyzed Thia-Michael
Addition Reaction to α,β‑Unsaturated Oxazolidin-2-one
Derivatives. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b03118
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AUTHORS (4)
SL
Samuel Lauzon
HK
Hoda Keipour
VG
Vincent Gandon
TO
Thierry Ollevier
KEYWORDS
Asymmetric Fe IIheterocyclicoxazolidin -2-one derivativesOxazolidinCatalyzed Thia-Michael Addition Reactionthia-Michael additionDerivativeMichael acceptorsUnusual hepta-coordinationstereoselectivitieenantioselective eventenantioselectivitieconstructionscopealiphatic thiolsβ- thioetherscarbonyl derivativesyieldchelationenantioselective Fe IImodelDFT calculations supportUnsaturated