Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives

• DOI: 10.1021/acs.orglett.7b03118
• Publication Date: 2017-11-20T13:01:08Z
• Authors: Samuel Lauzon; Hoda Keipour; Vincent Gandon; Thierry Ollevier
• Keywords: Michael reaction; Addition reaction

A highly enantioselective FeII-catalyzed thia-Michael addition to α,β-unsaturated carbonyl derivatives was developed. The scope of the reaction demonstrated with a selection aromatic, heterocyclic and aliphatic thiols, various Michael acceptors. corresponding β-thioethers were obtained in good excellent yields (up 98%) moderate enantioselectivities 96:4 er). Unusual hepta-coordination metal chelation oxazolidin-2-one allowed construction coherent model rationalizing event. DFT calculations support proposed for observed stereoselectivities.