Atroposelective Synthesis of Axially Chiral 3‑Arylindoles
by Copper-Catalyzed Asymmetric Cross-Coupling of Indoles with Quinones
and Naphthoquinones
Posted on 2020-06-17 - 16:07
A copper-catalyzed direct asymmetric
coupling of C2 sterically-hindering-group-substituted indoles with
quinone and naphthoquinone esters was developed by using the spirocyclic
pyrrolidine oxazoline (SPDO) ligand, which was accomplished by metal
catalysis for the first time. Diverse structures of axially chiral
3-arylindoles were obtained with good to high enantioselectivities
in good to high yields. This protocol can be expanded to implement
β-coupling with naphthoquinone esters, providing an alternative
way to prepare β-substituted derivatives of both naphthols and
naphthoquinones.
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Xi, Chao-Chao; Zhao, Xiao-Jing; Tian, Jin-Miao; Chen, Zhi-Min; Zhang, Kun; Zhang, Fu-Min; et al. (2020). Atroposelective Synthesis of Axially Chiral 3‑Arylindoles
by Copper-Catalyzed Asymmetric Cross-Coupling of Indoles with Quinones
and Naphthoquinones. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.0c01558
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AUTHORS (8)
CX
Chao-Chao Xi
XZ
Xiao-Jing Zhao
JT
Jin-Miao Tian
ZC
Zhi-Min Chen
KZ
Kun Zhang
FZ
Fu-Min Zhang
YT
Yong-Qiang Tu
JD
Jia-Wei Dong