Xu Feng Lin - Cochemist

Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis

Co-reporter:Lei Wang;Abdul Rahman;Xufeng Lin

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 28) pp:6033-6041

Publication Date(Web):2017/07/19

DOI:10.1039/C7OB01149K

A highly enantioselective aza-Friedel–Crafts reaction of N-sulfonyl cyclic ketimines with indoles catalyzed by chiral phosphoric acids has been developed. This methodology provides an efficient and facile route to indole-containing chiral cyclic α-amino acid derivatives bearing a quaternary stereocenter in high yields and up to 98% enantioselectivity.

Asymmetric synthesis of CF3- and indole-containing tetrahydro-β-carbolines via chiral spirocyclic phosphoric acid-catalyzed aza-Friedel–Crafts reaction

Co-reporter:En Xie;Abdul Rahman;Xufeng Lin

Organic Chemistry Frontiers 2017 vol. 4(Issue 7) pp:1407-1410

Publication Date(Web):2017/06/27

DOI:10.1039/C7QO00229G

An enantioselective aza-Friedel–Crafts alkylation reaction of indoles with 1-trifluoromethyl-3,4-dihydro-β-carbolines catalyzed by a chiral spirocyclic phosphoric acid has been realized. This methodology provides a facile route to 1-trifluoromethyl-1-indole-substituted tetrahydro-β-carbolines featuring a CF3-containing quaternary stereocenter in considerable yields and good enantioselectivities.

Organocatalytic Asymmetric Synthesis of Dihydrobenzoxazinones Bearing Trifluoromethylated Quaternary Stereocenters

Co-reporter:Hengqiao Lou, Yongtao Wang, Enze Jin, and Xufeng Lin

The Journal of Organic Chemistry 2016 Volume 81(Issue 5) pp:2019-2026

Publication Date(Web):February 16, 2016

DOI:10.1021/acs.joc.5b02848

Chiral phosphoric acid-catalyzed enantioselective aza-Friedel–Crafts reaction of trifluoromethyl benzoxazinones with pyrroles is reported. Under mild conditions, a range of enantioenriched dihydrobenzoxazinones bearing trifluoromethylated quaternary stereocenters could be obtained in good to excellent yield and ee. A remarkable fluorine effect is observed, and preliminary mechanistic studies combined with theory calculations suggest that triple-hydrogen-bonding interactions hold the transition structure rigidly and allow the bulky substituents of the catalyst to influence the enantioselectivity.

Triply Hydrogen-Bond-Directed Enantioselective Assembly of Pyrrolobenzo-1,4-diazine Skeletons with Quaternary Stereocenters

Co-reporter:Xiaoming Shen;Yongtao Wang;Tii Wu;Zhenjun Mao ; Xufeng Lin

Chemistry - A European Journal 2015 Volume 21( Issue 25) pp:9039-9043

Publication Date(Web):

DOI:10.1002/chem.201500823

Abstract

Highly efficient synthesis of optically enriched pyrrolobenzo-1,4-diazines bearing quaternary stereocenters has been realized through the chiral Brønsted acid-catalyzed Pictet–Spengler reaction of 2-(1H-pyrrol-1-yl)anilines and α-ketoamides in good to excellent yields and enantioselectivities. Computational studies suggest an unprecedented phenomenon whereby the chiral phosphoric acid catalyst employs attractive arene CH⋅⋅⋅N hydrogen bonding to activate the substrate and induce chirality through a triple hydrogen-bonding interaction.

Enantioselective synthesis of benzazepinoindoles bearing trifluoromethylated quaternary stereocenters catalyzed by chiral spirocyclic phosphoric acids

Co-reporter:Xuejian Li, Di Chen, Haorui Gu and Xufeng Lin

Chemical Communications 2014 vol. 50(Issue 56) pp:7538-7541

Publication Date(Web):22 May 2014

DOI:10.1039/C4CC02295E

The first highly enantioselective iso-Pictet–Spengler reaction of C-2-linked o-aminobenzylindoles with trifluoromethyl ketones was developed using chiral spirocyclic phosphoric acids as organocatalysts, which afforded optically active benzazepinoindoles bearing trifluoromethylated quaternary stereocenters.

Highly Enantioselective Synthesis of Dihydroquinazolinones Catalyzed by SPINOL-Phosphoric Acids

Co-reporter:Dan Huang, Xuejian Li, Fangxi Xu, Luhang Li, and Xufeng Lin

ACS Catalysis 2013 Volume 3(Issue 10) pp:2244

Publication Date(Web):September 6, 2013

DOI:10.1021/cs400591u

The asymmetric condensation/amine addition cascade sequence of 2-aminobenzamides and aldehydes catalyzed by chiral spirocyclic SPINOL-phosphoric acids was realized. SPINOL-phosphoric acid 1j was found to be a general, highly enantioselective organocatalyst for such cascade reactions at room temperature, affording 2,3-dihydroquinazolinones in excellent yields (up to 99%) with good to excellent ee’s (up to 98%). The best level of stereocontrol was obtained for aromatic aldehydes with an ortho substituent.Keywords: 2-aminobenzamide; asymmetric; dihydroquinazolinone; organocatalysis; phosphoric acid

Organocatalytic asymmetric multicomponent reactions of aromatic aldehydes and anilines with β-ketoesters: facile and atom-economical access to chiral tetrahydropyridines

Co-reporter:Xuejian Li, Yanyan Zhao, Haijun Qu, Zhenjun Mao and Xufeng Lin

Chemical Communications 2013 vol. 49(Issue 14) pp:1401-1403

Publication Date(Web):03 Jan 2013

DOI:10.1039/C2CC38349G

The first catalytic asymmetric pseudo five-component (AB2C2 type) reaction is reported. A spirocyclic chiral phosphoric acid catalyzed one-pot multicomponent reaction of aromatic aldehydes, anilines and β-ketoesters and afforded highly functionalized enantioenriched tetrahydropyridines with high levels of stereocontrol.

Highly enantioselective three-component Povarov reaction catalyzed by SPINOL-phosphoric acids

Co-reporter:Dan Huang, Fangxi Xu, Tao Chen, Yanguang Wang and Xufeng Lin

RSC Advances 2013 vol. 3(Issue 2) pp:573-578

Publication Date(Web):07 Nov 2012

DOI:10.1039/C2RA22796G

Chiral SPINOL-phosphoric acids exhibited high activities and excellent diastereo- and enantioselectivities in the catalysis of the three-component Povarov reaction of benzyl N-vinylcarbamate, anilines and aldehydes with a catalyst loading of 5 mol%. The synthetic utility of this protocol was demonstrated by the asymmetric synthesis of enantioenriched benzo[e]indolizidine with excellent yield and excellent level of sterecontrol.

Highly enantioselective hydrophosphonylation of imines catalyzed by SPINOL-phosphoric acid

Co-reporter:Yanyan Zhao, Xuejian Li, Fan Mo, Luhang Li and Xufeng Lin

RSC Advances 2013 vol. 3(Issue 29) pp:11895-11901

Publication Date(Web):02 May 2013

DOI:10.1039/C3RA40958A

Chiral SPINOL-phosphoric acid is a highly enantioselective organocatalyst for asymmetric hydrophosphonylation of cinnamaldehyde-derived aldimines with diethyl phosphite at room temperature, affording α-amino phosphonates in 85–98% yields and 80–98% ee.

A general access to 1,1-cyclopropane aminoketones and their conversion into 2-benzoyl quinolines

Co-reporter:Zhenjun Mao, Haijun Qu, Yanyan Zhao and Xufeng Lin

Chemical Communications 2012 vol. 48(Issue 79) pp:9927-9929

Publication Date(Web):20 Aug 2012

DOI:10.1039/C2CC35235D

1,1-Cyclopropane aminoketones were efficiently synthesized in high yields by the tandem reaction of α-amino aryl ketones with vinyl sulfonium salts using DBU as the base in CH2Cl2. This methodology was utilized to synthesize 2-benzoyl quinolines.

Highly enantioselective Biginelli reaction catalyzed by SPINOL-phosphoric acids

Co-reporter:Fangxi Xu, Dan Huang, Xufeng Lin and Yanguang Wang

Organic & Biomolecular Chemistry 2012 vol. 10(Issue 22) pp:4467-4470

Publication Date(Web):08 May 2012

DOI:10.1039/C2OB25663K

A highly enantioselective Biginelli reaction promoted by chiral spirocyclic SPINOL-phosphoric acids has been developed. Under the optimized conditions with 5 mol% catalyst loading, a wide range of optically active dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 98%) with good to excellent enantioselectivities (up to 99% ee). The synthetic utility of this method was demonstrated by the synthesis of chiral precursors of three drugs, including (S)-Monastrol, (S)-L-771688 and (S)-SQ 32926.

One-pot multicomponent synthesis of polysubstituted indolizines

Co-reporter:Zhenjun Mao, Xuejian Li, Xufeng Lin, Ping Lu, Yanguang Wang

Tetrahedron 2012 68(1) pp: 85-91

Publication Date(Web):

DOI:10.1016/j.tet.2011.10.083

Highly Enantioselective PictetSpengler Reaction Catalyzed by SPINOL-Phosphoric Acids

Co-reporter:Dan Huang;Fangxi Xu;Dr. Xufeng Lin;Dr. Yanguang Wang

Chemistry - A European Journal 2012 Volume 18( Issue 11) pp:3148-3152

Publication Date(Web):

DOI:10.1002/chem.201103207

A straightforward one-pot multicomponent synthesis of polysubstituted pyrroles

Co-reporter:Xufeng Lin, Zhenjun Mao, Xixiang Dai, Ping Lu and Yanguang Wang

Chemical Communications 2011 vol. 47(Issue 23) pp:6620-6622

Publication Date(Web):12 May 2011

DOI:10.1039/C1CC11363A

Polysubstituted pyrroles were efficiently synthesized in moderate yields by a one-pot multicomponent reaction starting from primary amines, ethyl glyoxalate and 2-bromoacetophenones in the presence of pyridine in refluxing acetonitrile. This methodology was utilized to synthesize a highly substituted benz[g]indole.

Molecular iodine-catalyzed and air-mediated tandem synthesis of quinolines via three-component reaction of amines, aldehydes, and alkynes

Co-reporter:Xuejian Li, Zhenjun Mao, Yanguang Wang, Weixiang Chen, Xufeng Lin

Tetrahedron 2011 67(21) pp: 3858-3862

Publication Date(Web):

DOI:10.1016/j.tet.2011.03.087

Facile synthesis of 1,2,4-triazolines via PPh3-triggered reaction of azodicarboxylate with 2-azidoacrylates

Co-reporter:Deng Hong, Yuanxun Zhu, Xufeng Lin, Yanguang Wang

Tetrahedron 2011 67(3) pp: 650-654

Publication Date(Web):

DOI:10.1016/j.tet.2010.11.043

Three-component reaction for the C2-functionalization of 1-substituted imidazoles with acetylenic ketones and isocyanates

Co-reporter:Yang Shen, Shuying Cai, Chi He, Xufeng Lin, Ping Lu, Yanguang Wang

Tetrahedron 2011 67(43) pp: 8338-8342

Publication Date(Web):

DOI:10.1016/j.tet.2011.08.069

Synthesis of Substituted Indoles from 2-Azidoacrylates and ortho-Silyl Aryltriflates†

Co-reporter:Deng Hong, Zhengbo Chen, Xufeng Lin, and Yanguang Wang

Organic Letters 2010 Volume 12(Issue 20) pp:4608-4611

Publication Date(Web):September 15, 2010

DOI:10.1021/ol101934v

2-Azidoacrylates react with benzynes in the presence of PPh3 and CsF to afford substituted indoles in good yields. The reaction involves the formation of iminophosphorane and benzyne and a subsequent double cyclization/hydrolysis/air-oxidation cascade. This methodology was utilized to synthesize 10H-indolo[1,2-a]indol-10-ones.

Copper-Catalyzed Tandem Nucleophilic Ring-Opening/Intramolecular Oxidative Amidation of N-Tosylaziridines and Hydrazones under Aerobic Conditions

Co-reporter:Deng Hong, Xufeng Lin, Yuanxun Zhu, Ming Lei and Yanguang Wang

Organic Letters 2009 Volume 11(Issue 24) pp:5678-5681

Publication Date(Web):November 19, 2009

DOI:10.1021/ol902376w

A novel and efficient copper-catalyzed tandem reaction of N-tosylaziridines and hydrazones under aerobic conditions to afford the functionalized tetrahydrotriazines is described. The process involves a nucleophilic ring-opening and an intramolecular oxidative amidation.

Palladium on Charcoal as a Recyclable Catalyst for CS Cross-Coupling of Thiols with Aryl Halides under Ligand-Free Conditions

Co-reporter:Zheng Jiang;Jin She ;Xufeng Lin

Advanced Synthesis & Catalysis 2009 Volume 351( Issue 16) pp:2558-2562

Publication Date(Web):

DOI:10.1002/adsc.200900501

Abstract

S-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides using a catalytic amount of palladium on charcoal as a heterogeneous catalysis with potassium hydroxide as the base in dimethyl sulfoxide (DMSO) at 110 °C is accomplished in good yields. The CS bond formation reaction functions under ligand-free conditions, and the palladium on charcoal catalyst can be is reused for five runs without any loss of activity.

Total synthesis of glypetelotine

Co-reporter:Xiang Hong Huang, Xu Feng Lin, Su Qin Chen, Yan Guang Wang

Chinese Chemical Letters 2009 Volume 20(Issue 6) pp:643-644

Publication Date(Web):June 2009

DOI:10.1016/j.cclet.2009.02.005

A total synthesis of glypetelotine, the first sulphur-containing indole alkaloid from the leaf extracts of Glycosmis petelotii collected in the north of Vietnam, was described from indole through 6 steps. The structure of the glypetelotine was confirmed by IR, 1H NMR, 13C NMR and MS analysis. The spectral data of synthetic compound was identical with those of natural compound.

Molecular iodine-catalyzed C3-alkylation of 4-hydroxycoumarins with secondary benzyl alcohols

Co-reporter:Xufeng Lin, Xixiang Dai, Zhenjun Mao, Yanguang Wang

Tetrahedron 2009 65(45) pp: 9233-9237

Publication Date(Web):

DOI:10.1016/j.tet.2009.09.007

A general access to 1,1-cyclopropane aminoketones and their conversion into 2-benzoyl quinolines

Co-reporter:Zhenjun Mao, Haijun Qu, Yanyan Zhao and Xufeng Lin

Chemical Communications 2012 - vol. 48(Issue 79) pp:NaN9929-9929

Publication Date(Web):2012/08/20

DOI:10.1039/C2CC35235D

1,1-Cyclopropane aminoketones were efficiently synthesized in high yields by the tandem reaction of α-amino aryl ketones with vinyl sulfonium salts using DBU as the base in CH2Cl2. This methodology was utilized to synthesize 2-benzoyl quinolines.

Enantioselective synthesis of benzazepinoindoles bearing trifluoromethylated quaternary stereocenters catalyzed by chiral spirocyclic phosphoric acids

Co-reporter:Xuejian Li, Di Chen, Haorui Gu and Xufeng Lin

Chemical Communications 2014 - vol. 50(Issue 56) pp:NaN7541-7541

Publication Date(Web):2014/05/22

DOI:10.1039/C4CC02295E

The first highly enantioselective iso-Pictet–Spengler reaction of C-2-linked o-aminobenzylindoles with trifluoromethyl ketones was developed using chiral spirocyclic phosphoric acids as organocatalysts, which afforded optically active benzazepinoindoles bearing trifluoromethylated quaternary stereocenters.

Organocatalytic asymmetric multicomponent reactions of aromatic aldehydes and anilines with β-ketoesters: facile and atom-economical access to chiral tetrahydropyridines

Co-reporter:Xuejian Li, Yanyan Zhao, Haijun Qu, Zhenjun Mao and Xufeng Lin

Chemical Communications 2013 - vol. 49(Issue 14) pp:NaN1403-1403

Publication Date(Web):2013/01/03

DOI:10.1039/C2CC38349G

The first catalytic asymmetric pseudo five-component (AB2C2 type) reaction is reported. A spirocyclic chiral phosphoric acid catalyzed one-pot multicomponent reaction of aromatic aldehydes, anilines and β-ketoesters and afforded highly functionalized enantioenriched tetrahydropyridines with high levels of stereocontrol.

Highly enantioselective Biginelli reaction catalyzed by SPINOL-phosphoric acids

Co-reporter:Fangxi Xu, Dan Huang, Xufeng Lin and Yanguang Wang

Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 22) pp:NaN4470-4470

Publication Date(Web):2012/05/08

DOI:10.1039/C2OB25663K

A highly enantioselective Biginelli reaction promoted by chiral spirocyclic SPINOL-phosphoric acids has been developed. Under the optimized conditions with 5 mol% catalyst loading, a wide range of optically active dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 98%) with good to excellent enantioselectivities (up to 99% ee). The synthetic utility of this method was demonstrated by the synthesis of chiral precursors of three drugs, including (S)-Monastrol, (S)-L-771688 and (S)-SQ 32926.

Asymmetric synthesis of CF3- and indole-containing tetrahydro-β-carbolines via chiral spirocyclic phosphoric acid-catalyzed aza-Friedel–Crafts reaction

Co-reporter:En Xie, Abdul Rahman and Xufeng Lin

Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 7) pp:NaN1410-1410

Publication Date(Web):2017/04/17

DOI:10.1039/C7QO00229G

An enantioselective aza-Friedel–Crafts alkylation reaction of indoles with 1-trifluoromethyl-3,4-dihydro-β-carbolines catalyzed by a chiral spirocyclic phosphoric acid has been realized. This methodology provides a facile route to 1-trifluoromethyl-1-indole-substituted tetrahydro-β-carbolines featuring a CF3-containing quaternary stereocenter in considerable yields and good enantioselectivities.

A straightforward one-pot multicomponent synthesis of polysubstituted pyrroles

Co-reporter:Xufeng Lin, Zhenjun Mao, Xixiang Dai, Ping Lu and Yanguang Wang

Chemical Communications 2011 - vol. 47(Issue 23) pp:NaN6622-6622

Publication Date(Web):2011/05/12

DOI:10.1039/C1CC11363A

Polysubstituted pyrroles were efficiently synthesized in moderate yields by a one-pot multicomponent reaction starting from primary amines, ethyl glyoxalate and 2-bromoacetophenones in the presence of pyridine in refluxing acetonitrile. This methodology was utilized to synthesize a highly substituted benz[g]indole.

Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis

Co-reporter:Lei Wang, Abdul Rahman and Xufeng Lin

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 28) pp:NaN6041-6041

Publication Date(Web):2017/06/26

DOI:10.1039/C7OB01149K

A highly enantioselective aza-Friedel–Crafts reaction of N-sulfonyl cyclic ketimines with indoles catalyzed by chiral phosphoric acids has been developed. This methodology provides an efficient and facile route to indole-containing chiral cyclic α-amino acid derivatives bearing a quaternary stereocenter in high yields and up to 98% enantioselectivity.