Asymmetric Fe II -Catalyzed Thia-Michael addition reaction to α,β-unsaturated Oxazolidin-2-one Derivatives

Authors: Lauzon, SamuelKeipour, Hoda; Gandon, Vincent; Ollevier, Thierry
Abstract: 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.
Document Type: Article de recherche
Issue Date: 20 November 2017
Open Access Date: 20 November 2018
Document version: AM
Permalink: http://hdl.handle.net/20.500.11794/17142
This document was published in: Organic letters, Vol. 19 (23), 6324-6327 (2017)
https://doi.org/10.1021/acs.orglett.7b03118
American Chemical Society
Alternative version: 10.1021/acs.orglett.7b03118
Collection:Articles publiés dans des revues avec comité de lecture

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