Journal
ORGANIC LETTERS
Volume 19, Issue 23, Pages 6324-6327Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03118
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Centre in Green Chemistry and Catalysis (CGCC)
- Universite Laval
- NSERC
- FRQNT
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A highly enantioselective Fe-II-catalyzed thia-Michael addition to alpha,beta-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 beta-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 alpha,beta-unsaturated oxazolidin-2-one derivatives allowed the construction of a coherent model rationalizing the enantios elective event. DFT calculations support the proposed model for observed stereoselectivities.
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