Enantioselective Arylation of Tetrasubstituted Enamines: Access to Enantioenriched Indolenine and 1H-Indole Derivatives

被引：13

作者：

Liang, Ren-Xiao ^{[1
]}

Zhong, Chao ^{[1
]}

Liu, Zhi-Hong ^{[1
]}

Yang, Miao ^{[1
]}

Tang, Heng-Wei ^{[1
]}

Chen, Jian-Fei ^{[1
]}

Yang, Yun-Fang ^{[1
]}

Jia, Yi-Xia ^{[1
,2
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310014, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ACS CATALYSIS | 2021年 / 11卷 / 03期

基金：

中国国家自然科学基金;

关键词：

enamines; palladium; arylation; indolenines; asymmetric catalysis; CATALYTIC ASYMMETRIC DEAROMATIZATION; ALLYLIC DEAROMATIZATION; FUNCTIONALIZED INDOLES; DIRECT ANNULATION; DESYMMETRIZATION; CONSTRUCTION; ALKALOIDS;

D O I：

10.1021/acscatal.0c05020

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Palladium-catalyzed intramolecular enantioselective beta-arylation of tetrasubstituted endocyclic and exocyclic enamines is developed. A range of optically active medium-ring fused indolenines or 3,3'-spiroindolenines were achieved in enantiomeric ratios up to 98:2 with Cs2CO3 or K3PO4 as the base in the presence of chiral PHOX ligands. The use of Ag3PO4 as a base led to enantioenriched 1H-indoles in good enantiomeric ratios (up to 89:11) with (S)-DIFLUORPHOS as a chiral ligand, which proceeded via a possible domino enamine-isomerization/beta-arylation sequence.

引用

页码：1827 / 1832

页数：6

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