Xiang Wu

Name:

Organization: University of Science and Technology of China

Department: Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry

Title:

Chemicals
References

Synthesis of Polycyclic Amines through Mild Metal-Free Tandem Cross-Dehydrogenative Coupling/Intramolecular Hydroarylation of N-Aryltetrahydroisoquinolines and Crotonaldehyde

Co-reporter:Xiang Wu;Dian-Feng Chen;Shu-Sen Chen ;Yi-Fan Zhu

European Journal of Organic Chemistry 2015 Volume 2015( Issue 3) pp:468-473

Publication Date(Web):

DOI:10.1002/ejoc.201403375

Abstract

A [4+2] cycloaddition reaction proceeding through tandem cross-dehydrogenative coupling/intramolecular hydroarylation between N-aryltetrahydroisoquinolines and crotonaldehyde was developed by virtue of enamine–iminium catalysis, which enabled the rapid construction of ring-fused tetrahydroquinolines. The first metal-free catalytic oxidative coupling of γ-selective C(sp³)–H bonds of crotonaldehyde was realized by using a secondary amine catalyst and 2,3-dichloro-5,6-dicyanoquinone.

Chiral Brønsted acid catalyzed intermolecular Friedel–Crafts alkylation of styrenes with indoles: construction of all-carbon quaternary stereocenters

Co-reporter:Ming-Li Li, Dian-Feng Chen, Shi-Wei Luo, Xiang Wu

Tetrahedron: Asymmetry 2015 Volume 26(Issue 4) pp:219-224

Publication Date(Web):28 February 2015

DOI:10.1016/j.tetasy.2015.01.005

A chiral Brønsted acid catalyzed Friedel–Crafts reaction of terminal 1,1-diaryalkenes with indoles is described. This reaction provides indole derivatives with acyclic all-carbon quaternary stereocenters in excellent yields and with excellent enantioselectivities, and features high atom efficiency without the generation of side products.(S)-2-(1-(1H-Indol-3-yl)-1-(4-methoxyphenyl)ethyl)phenolC23H21NO2[α]D25 = +23.1 (c 0.74, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(5-Methoxy-1H-indol-3-yl)-1-(4-methoxyphenyl)ethyl)phenolC24H23NO3[α]D25 = +45.3 (c 0.70, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(4-Methoxyphenyl)-1-(5-methyl-1H-indol-3-yl)ethyl)phenolC24H23NO2[α]D25 = +27.2 (c 0.71, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(5-Chloro-1H-indol-3-yl)-1-(4-methoxyphenyl)ethyl)phenolC23H20ClNO2[α]D25 = +28.8 (c 0.60, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(5-Bromo-1H-indol-3-yl)-1-(4-methoxyphenyl)ethyl)phenolC23H20BrNO2[α]D25 = +37.9 (c 0.83, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(4-Methoxyphenyl)-1-(5-nitro-1H-indol-3-yl)ethyl)phenolC23H20N2O4[α]D25 = +50.5 (c 0.66, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(6-Fluoro-1H-indol-3-yl)-1-(4-methoxyphenyl)ethyl)phenolC23H20FNO2[α]D25 = +15.2 (c 0.60, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(6-Chloro-1H-indol-3-yl)-1-(4-methoxyphenyl)ethyl)phenolC23H20ClNO2[α]D25 = +19.6 (c 0.56, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(4-Methoxyphenyl)-1-(6-methyl-1H-indol-3-yl)ethyl)phenolC24H23NO2[α]D25 = +15.1 (c 0.53, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(4-Methoxyphenyl)-1-(7-methyl-1H-indol-3-yl)ethyl)phenolC24H23NO2[α]D25 = +28.3 (c 0.54, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(4-((tert-Butyldimethylsilyl)oxy)phenyl)-1-(1H-indol-3-yl)ethyl)phenolC28H33NO2Si[α]D25 = +12.2 (c 0.37, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(4-(Benzyloxy)phenyl)-1-(1H-indol-3-yl)ethyl)phenolC29H25NO2[α]D25 = +14.9 (c 0.71, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(Benzo[d][1,3]dioxol-5-yl)-1-(1H-indol-3-yl)ethyl)phenolC23H19NO3[α]D25 = +35.8 (c 0.52, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(1H-Indol-3-yl)-1-(4-methoxyphenyl)ethyl)-4-methoxyphenolC24H23NO3[α]D25 = +20.3 (c 0.37, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(1H-Indol-3-yl)-1-phenylethyl)-4-methoxyphenolC23H21NO2[α]D25 = +23.1 (c 0.59, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(1H-Indol-3-yl)-1-(4-methoxyphenyl)ethyl)-4-fluorophenolC23H20FNO2[α]D25 = +22.1 (c 0.33, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(1H-Indol-3-yl)-1-(4-methoxyphenyl)ethyl)-5-fluorophenolC23H20FNO2[α]D25 = +16.9 (c 0.49, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(1H-Indol-3-yl)-1-(4-methoxyphenyl)ethyl)-5-methylphenolC24H23NO2[α]D25 = +28.3 (c 0.42, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(4-(Dimethylamino)phenyl)-1-(1H-indol-3-yl)ethyl)phenolC24H24N2O[α]D25 = +22.1 (c 0.14, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(1H-Indol-3-yl)-1-(6-methoxynaphthalen-2-yl)ethyl)phenolC27H23NO2[α]D25 = +13.1 (c 0.51, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)(S)-2-(1-(1H-Indol-3-yl)-1-(4-methoxyphenyl)ethyl)naphthalen-1-olC27H23NO2[α]D25 = −6.4 (c 0.50, CHCl3)Source of chirality: Enantioselective synthesisAbsolute configuration: (S)

Enantioselective Construction of [6,5,6]-Carbocyclic Systems by Organo/Metal-Catalyzed Sequential Reactions

Co-reporter:Xiang Wu, Ming-Li Li, Dian-Feng Chen, and Shu-Sen Chen

The Journal of Organic Chemistry 2014 Volume 79(Issue 10) pp:4743-4750

Publication Date(Web):April 17, 2014

DOI:10.1021/jo5006729

An efficient strategy for the enantioselective construction of [6,5,6]-carbocyclic compounds has been established via one-pot reaction of (E)-4-(2-ethynylphenyl)but-3-en-2-ones with maleimide sequentially catalyzed by cinchona alkaloid-based primary amine and gold complex (Ph3PAuNTf2). This methodology provided a facile approach to access the [6,5,6]-tricyclic skeleton in fairly good yield and with perfect enantioselectivities (98% to >99% ee).

Hybrid Gold/Chiral Brønsted Acid Relay Catalysis Allows an Enantioselective Synthesis of (−)-5-epi-Eupomatilone-6

Co-reporter:Xiang Wu, Ming-Li Li, and Pu-sheng Wang

The Journal of Organic Chemistry 2014 Volume 79(Issue 1) pp:419-425

Publication Date(Web):December 12, 2013

DOI:10.1021/jo4024232

An enantioselective synthesis of (−)-5-epi-eupomatilone-6 has been accomplished by using relay catalytic cascade intramolecular hydrosiloxylation and Mukaiyama aldol reaction of 2,3,4-trimethoxy-6-(phenylethynyl)phenyl dimethylsilanol with fluorenylglyoxylate.