Enantioselective aza-Friedel-Crafts reaction of furan with α-ketimino esters induced by a conjugated double hydrogen bond network of chiral bis(phosphoric acid) catalysts

被引：59

作者：

Hatano, Manabu ^{[1
]}

Okamoto, Haruka ^{[1
]}

Kawakami, Taro ^{[1
]}

Toh, Kohei ^{[1
]}

Nakatsuji, Hidefumi ^{[1
]}

Sakakura, Akira ^{[2
]}

Ishihara, Kazuaki ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Furo Cho, Nagoya, Aichi 4648603, Japan

[2] Okayama Univ, Grad Sch Nat Sci & Technol, Kita Ku, 3-1-1 Tsushimanaka, Okayama 7008530, Japan

来源：

CHEMICAL SCIENCE | 2018年 / 9卷 / 30期

关键词：

MANNICH-TYPE REACTION; STRONGER BRONSTED ACIDS; DIELS-ALDER REACTIONS; PHOSPHORIC-ACID; 1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC CATALYSIS; AMINO-ACIDS; AZOMETHINE YLIDES; DICARBOXYLIC-ACID; RECENT PROGRESS;

D O I：

10.1039/c8sc02290a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral C-2- and C-1-symmetric BINOL-derived bis(phosphoric acid) catalysts, which have OP(=O)(OH)(2)/OP(=O)(OH)(OR) moieties at the 2,2 0 - positions, were developed and used for the enantioselective azaFriedel-Crafts reaction of 2-methoxyfuran with alpha-ketimino esters for the first time. The intramolecular conjugated double hydrogen bond network is a key to increasing the Bronsted acidity and preventing deactivation of the catalysts. Highly functionalized alpha-amino acid derivatives with a chiral quaternary carbon center could be transformed into versatile optically active N- and O-heterocycles and an a- arylsubstituted serine.

引用

页码：6361 / 6367

页数：7

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