Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

Yang，Kai1; Lou，Yixian2; Wang，Chenglan2; Qi，Liang Wen3; Fang，Tongchang1; Zhang，Feng1; Xu，Hetao1; Zhou，Lu1; Li，Wangyang1; Zhang，Guan4; Yu，Peiyuan3; Song，Qiuling1,2,4

2020-02-17

10.1002/anie.201913656

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

A new chiral Brønsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.

asymmetric catalysis boron Brønsted acid heterocycles water

SCI ; IC ; CCR ; EI

英语

NI期刊

通讯

Southern University of Science and Technology[] ; National Natural Science Foundation of China[21772046]

Chemistry

Chemistry, Multidisciplinary

WOS:000506262700001

Wiley-VCH Verlag

20200308039026

Boron ; Density functional theory ; Water

Nonferrous Metals and Alloys excluding Alkali and Alkaline Earth Metals:549.3 ; Inorganic Compounds:804.2 ; Probability Theory:922.1

CHEMISTRY

2-s2.0-85077846231

Scopus

1.Key Laboratory of Molecule Synthesis and Function Discovery,Fujian Province University,College of Chemistry at Fuzhou University,Fujian,Fuzhou,350108,China
2.Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals,Zhejiang University of Technology,Hangzhou,310000,China
3.Department of Chemistry and Shenzhen Grubbs Institute,Southern University of Science and Technology,Shenzhen,518055,China
4.Institute of Next Generation Matter Transformation,College of Materials Science Engineering at Huaqiao University,Xiamen,668 Jimei Boulevard,361021,China

Yang，Kai,Lou，Yixian,Wang，Chenglan,et al. Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2020,59(8):3294-3299.

Yang，Kai.,Lou，Yixian.,Wang，Chenglan.,Qi，Liang Wen.,Fang，Tongchang.,...&Song，Qiuling.(2020).Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,59(8),3294-3299.

Yang，Kai,et al."Chiral Brønsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59.8(2020):3294-3299.