TY - JOUR
T1 - Enantioselective Au(I)/Au(III) Redox Catalysis Enabled by Chiral (P,N)-Ligands
AU - Chintawar, Chetan C.
AU - Bhoyare, Vivek W.
AU - Mane, Manoj Vasisht
AU - Patil, Nitin T.
N1 - KAUST 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.
PY - 2022/4/18
Y1 - 2022/4/18
N2 - 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
AB - 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
UR - http://hdl.handle.net/10754/676330
UR - https://pubs.acs.org/doi/10.1021/jacs.2c02799
U2 - 10.1021/jacs.2c02799
DO - 10.1021/jacs.2c02799
M3 - Article
C2 - 35436097
SN - 0002-7863
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
ER -