Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 16, Pages 7089-7095Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c02799
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Funding
- Science and Engineering Research Board (SERB), New Delhi [DIA/2018/000016, EMR/2016/007177]
- UGC
- CSIR
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The first report of enantioselective Au(I)/Au(III) redox catalysis using a newly designed hemilabile chiral (P,N)-ligand (ChetPhos) is presented. This concept has been demonstrated by the development of enantioselective 1,2-oxyarylation and 1,2-aminoarylation reactions, providing direct access to medicinally relevant compounds with high yields and enantioselectivities.
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 C-2-symmetric chiral environment present around nitrogen, imparting a high level of enantioselectivity.
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