期刊
ORGANIC LETTERS
卷 23, 期 4, 页码 1181-1187出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03827
关键词
-
资金
- National Natural Science Foundation of China [21602231]
- Natural Science Foundation of Jiangsu Province [BK20191197]
Central-to-axial chirality transfer via C-N single bond oxidation was achieved for the first time, leading to the preparation of a new family of axially chiral heteroaromatic biaryl backbones and P,N-ligands. Two atropisomers of Quinoxalinaps could be easily obtained from the same precursor enantiomer through a simple dehydrogenative oxidation. Phosphine could be introduced into the ligands before or after the chirality control process.
Central-to-axial chirality transfer via C-N single bond oxidation was first achieved as a versatile and conceptually distinct strategy to prepare a new family of axially chiral heteroaromatic biaryl backbones and P,N-ligands (named as Quinoxalinaps) in gram scale. Two atropisomers of Quinoxalinaps (ee >99%) were readily accessed from the same precursor enantiomer by a simple dehydrogenative oxidation with MnO2 and t-BuOOH under mild conditions. Phosphine could be introduced into the ligands before or after the chirality control process. Moreover, these Quinoxalinap P,N-ligands performed well for both asymmetric reactions of the CuBr-catalyzed alkyne conjugate addition with up to -94% ee and AgOAc-catalyzed glycinate imine [3 + 2] annulation with 90% ee, respectively.
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