Enantioselective Friedel-Crafts Alkylation Reaction of Indoles with α-Trifluoromethylated β-Nitrostyrenes Catalyzed by Chiral BINOL Metal Phosphate

被引：47

作者：

Ibanez, Ignacio ^{[1
]}

Kaneko, Mio ^{[1
]}

Kamei, Yuto ^{[2
]}

Tsutsumi, Ryosuke ^{[2
]}

Yamanaka, Masahiro ^{[1
,2
]}

Akiyama, Takahiko ^{[1
]}

机构：

[1] Gakushuin Univ, Dept Chem, Fac Sci, Toshima Ku, 1-5-1 Mejiro, Tokyo 1718588, Japan

[2] Rikkyo Univ, Dept Chem, Fac Sci, Toshima Ku, 3-41-1 Nishi Ikebukuro, Tokyo 1718501, Japan

来源：

ACS CATALYSIS | 2019年 / 9卷 / 08期

关键词：

Indole; Friedel-Crafts alkylation; nitroalkene; metal chiral phosphate; quaternary carbon center; CARBON QUATERNARY STEREOCENTERS; ASYMMETRIC-SYNTHESIS; PHOSPHORIC-ACID; BRONSTED ACID; STEREOSELECTIVE CONSTRUCTION; DENSITY FUNCTIONALS; NATURAL-PRODUCTS; CALCIUM; PHARMACEUTICALS; DERIVATIVES;

D O I：

10.1021/acscatal.9b01811

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：

An efficient enantioselective Friedel-Crafts alkylation reaction of indoles with alpha-CF3-substituted beta-nitrostyrenes is disclosed. The key to success is the use of a chiral calcium BINOL bis(phosphate) complex as a Lewis acid catalyst. The reaction gives access to a wide variety of optically active indoles bearing trifluoromethylated all-carbon quaternary stereocenter (up to 20 examples) in high yields (up to 99%) with excellent enantioselectivities (up to 98%) under mild reaction conditions. Non activated alpha-alkyl-beta-nitrostyrenes also participated in the Friedel-Crafts alkylation reaction successfully.

引用

页码：6903 / 6909

页数：13

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