Presented herein is the first report of enantioselective Au(I)/Au(III) redox catalysis, enabled by a newly designed hemilabile chiral (P,N)-ligand (ChetPhos). The potential of this concept has been demonstrated by the development of enantioselective 1,2-oxyarylation and 1,2-aminoarylation of alkenes which provided direct access to the medicinally relevant 3-oxy- and 3-aminochromans (up to 88% yield and 99% ee). DFT studies were carried out to unravel the enantiodetermining step, which revealed that the stronger trans influence of phosphorus allows selective positioning of the substrate in the C2-symmetric chiral environment present around nitrogen, imparting a high level of enantioselectivity
Bibliographical noteKAUST Repository Item: Exported on 2022-04-21
Acknowledgements: Generous financial support by the Science and Engineering Research Board (SERB), New Delhi (File Nos. DIA/2018/000016 and EMR/2016/007177), is gratefully acknowledged. C.C.C. and V.W.B. thank the UGC and CSIR, respectively, for the award of Senior Research Fellowships. We thank Abhik Paul from IISERB for his assistance with SC-XRD analysis.
ASJC Scopus subject areas
- Colloid and Surface Chemistry
- General Chemistry