Jin-Tao Liu

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Name: 刘金涛; JinTao Liu

Organization: Chinese Academy of Sciences , China

Department: Shanghai Institute of Organic Chemistry

Title: Researcher/Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Per(poly)fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction

Co-reporter:Peng Li, Li-Juan Liu and Jin-Tao Liu

Organic & Biomolecular Chemistry 2011 vol. 9(Issue 1) pp:74-77

Publication Date(Web):17 Nov 2010

DOI:10.1039/C0OB00699H

A highly diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction assisted by per(poly)fluoro-alkanesulfinamides is presented, providing a broad spectrum of highly functionalized piperidine derivatives with excellent endo/exo and facial diastereoselectivities. The electron-withdrawing perfluoroalkyl groups are crucial for the success of this reaction under mild conditions and facilitate monitoring the process and stereoselectivities of the reaction. The synthetic potential of these cycloadducts is also highlighted.

2-Chlorotetrafluoroethanesulfinamide Induced Diastereoselective Three-Component Aminoallylation of Aldehydes

Co-reporter:Lijuan Liu ;Jintao Liu

Chinese Journal of Chemistry 2011 Volume 29( Issue 12) pp:2722-2726

Publication Date(Web):

DOI:10.1002/cjoc.201100134

Abstract

The diastereoselective three-component reaction of aldehydes, allyl bromide, and (S)-2-chlorotetrafluoroethanesulfinamide was achieved in the presence of zinc powder and titanium(IV) isopropoxide. Compared to (S)-tert-butanesulfinamide, the reaction used zinc powder instead of indium and better results were obtained with aromatic aldehydes. Moreover, opposite stereoselectivity is observed.

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) Catalyzed Regiospecific and Diastereoselective Reaction of Chiral N-(tert-Butanesulfinyl)ketimines and ,-Unsaturated Trifluoromethyl Ketones

Co-reporter:Fan Zhang;Zhenjiang Liu;Jintao Liu

Chinese Journal of Chemistry 2011 Volume 29( Issue 12) pp:2727-2731

Publication Date(Web):

DOI:10.1002/cjoc.201100133

Abstract

The reaction of chiral N-(tert-butanesulfinyl)ketimines and α,β-unsaturated trifluoromethyl ketones catalyzed by DBU was achieved under mild conditions. 1,2-Addition products, precursors of chiral trifluoromethylated 1,3-amino alcohols, were obtained diastereoselectively (dr value up to 95:5) in moderate yields (up to 76%). A possible catalytic cycle was proposed.

A facile method to construct cyclic α,α-difluoromethylenephosphonate—A novel cyclic phosphate mimic

Co-reporter:Yun Lin, Jin-Tao Liu

Journal of Fluorine Chemistry 2011 Volume 132(Issue 5) pp:310-317

Publication Date(Web):May 2011

DOI:10.1016/j.jfluchem.2011.02.014

A facile and efficient synthesis of cyclic α,α-difluoromethylenephosphonates by halogen-induced intramolecular cyclization of β-allenic α,α-difluoromethylenephosphonates is described. The protocol gives multi-substituted six-membered phosphonates with high regioselectivity, providing a new entry to the cyclic phosphate mimics which is still an unexplored but promising area.Graphical abstractAn efficient synthesis of six-membered α,α-difluoromethylenephosphonates as biologically interesting cyclic phosphate mimics in good yields has been described.Highlights► Design of novel cyclic phosphate mimic—six-membered α,α-difluoromethylenephosphonates. ► Mild hydrolysis reaction condition without destroying the allenic moiety. ► High regioselectivity and yield of the resulted cyclic α,α-difluoromethylenephosphonates. ► The possibility to incorporate this novel subunit into other molecules with potential bioactivities with the presence of vinyl iodine/bromine in the product.

Michael addition of N-sulfinyl metalloenamines to β-trifluoromethyl-α,β-unsaturated ester: an efficient access to chiral 4-trifluoromethyl-2-piperidones

Co-reporter:Fan Zhang, Zhen-Jiang Liu, Jin-Tao Liu

Tetrahedron 2010 66(34) pp: 6864-6868

Publication Date(Web):

DOI:10.1016/j.tet.2010.06.047

Iodocyclization of trifluoromethylallenic phosphonates: an efficient approach to trifluoromethylated oxaphospholenes

Co-reporter:Peng Li, Zhen-Jiang Liu, Jin-Tao Liu

Tetrahedron 2010 66(51) pp: 9729-9732

Publication Date(Web):

DOI:10.1016/j.tet.2010.10.040

Reaction of Perfluoroalkanesulfinyl Chlorides with Enamines: A Facile Synthesis of -Perfluoroalkanesulfinyl Ketones and Aldehydes

Co-reporter:Xiaobo LI;Lingjun CHEN;Xiaojin WANG ;Jintao LIU

Chinese Journal of Chemistry 2009 Volume 27( Issue 1) pp:151-156

Publication Date(Web):

DOI:10.1002/cjoc.200990008

Abstract

The reaction of perfluoroalkanesulfinyl chlorides with enamines was achieved in the presence of triethylamine, and α-perfluoroalkanesulfinyl carbonyl compounds were obtained in moderate to good yields after hydrolysis of the reaction intermediates with dilute hydrochloric acid.

The addition of perfluoroalkanesulfinyl chlorides to alkoxyallenes

Co-reporter:Ling-Jun Chen, Jin-Tao Liu

Journal of Fluorine Chemistry 2009 Volume 130(Issue 3) pp:329-331

Publication Date(Web):March 2009

DOI:10.1016/j.jfluchem.2008.12.007

The addition reaction of perfluoroalkanesulfinyl chlorides to alkoxyallenes was achieved under mild conditions. Two kinds of perfluoroalkyl alkenyl sulfoxides, β-alkoxyvinyl perfluoroalkyl sulfoxides and α-perfluoroalkanesulfinyl enones or enals, were obtained selectively depending on the structure of alkoxyallenes.Perfluoroalkanesulfinyl chlorides reacted with alkoxyallenes under mild conditions to give two kinds of perfluoroalkyl alkenyl sulfoxides selectively depending on the structure of alkoxyallenes.

Organic base catalyzed carbonyl allylation of methyl trifluoropyruvate with activated alkenes

Co-reporter:Fan Zhang, Xiao-Jin Wang, Chen-Xin Cai, Jin-Tao Liu

Tetrahedron 2009 65(1) pp: 83-86

Publication Date(Web):

DOI:10.1016/j.tet.2008.11.002

Asymmetric synthesis of either diastereomer of trifluoromethylated allylic amines by the selective reduction of trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketoimines

Co-reporter:Zhen-Jiang Liu and Jin-Tao Liu

Chemical Communications 2008 (Issue 41) pp:5233-5235

Publication Date(Web):12 Sep 2008

DOI:10.1039/B810459J

Regio- and diastereoselective reduction of chiraltrifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketoimines 1 was achieved by choosing appropriate reducing agent and either diastereomer of the corresponding trifluoromethylated allylic amines was obtained with good yield and excellent diastereoselectivity (up to >99 : 1 dr).

One-pot Synthesis of 4-Trifluoromethyl-1,2-dihydropyrimidines

Co-reporter:Yun Lin;Xian-Jin Yang

Chinese Journal of Chemistry 2007 Volume 25(Issue 1) pp:

Publication Date(Web):8 JAN 2007

DOI:10.1002/cjoc.200790003

4-Trifluoromethyl-1,2-dihydropyrimidines were synthesized in moderate yields by the one-pot reaction of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one, aldehydes and ammonia catalyzed by zinc chloride under mild conditions.

Unusual Cycloadducts from the Dipolar Cycloaddition of Allenyl Perfluoroalkyl Sulfones to Nitrones

Co-reporter:Xiao-Jin Wang

Chinese Journal of Chemistry 2007 Volume 25(Issue 5) pp:

Publication Date(Web):11 MAY 2007

DOI:10.1002/cjoc.200790121

The dipolar cycloaddition reaction of allenyl perfluoroalkyl sulfones (1) to nitrones (2) was described. Unlike nonfluorine-containing allenyl sulfones, 1 reacted readily with 2 in ether at room temperature and unusual zwitterionic cycloadducts (3) were obtained in good yields due to the strong electron-withdrawing effect of perfluoroalkyl groups. The structure of 3 was characterized by spectral analyses and X-ray crystallography.

Convenient synthesis of β-allenic α-difluoromethylenephosphonic acid monoesters: Potential synthons for cyclic phosphate mimics

Co-reporter:Yun Lin, Jin Tao Liu

Chinese Chemical Letters 2007 Volume 18(Issue 1) pp:33-36

Publication Date(Web):January 2007

DOI:10.1016/j.cclet.2006.11.029

β-Allenic α-difluoromethylenephosphonic acid monoesters were prepared under mild conditions for the first time by hydrolyzing the corresponding diethyl phosphonates in aqueous sodium hydroxide solution.

Reaction of Alkanesulfinyl Chloride with Grignard Reagents: a Convenient Synthesis of Alkyl Sulfoxides

Co-reporter:Xiao-Bo Li

Chinese Journal of Chemistry 2007 Volume 25(Issue 9) pp:1309-1311

Publication Date(Web):17 SEP 2007

DOI:10.1002/cjoc.200790243

Alkyl sulfoxides were synthesized in good yields from the reaction of alkanesulfinyl chloride with Grignard reagents in the presence of zinc chloride.

Conjugate Additions of Secondary Amines and Water to Allenyl Perfluoroalkyl Sulfones

Co-reporter:Xiao-Jin Wang;Yun Lin

Chinese Journal of Chemistry 2006 Volume 24(Issue 6) pp:775-780

Publication Date(Web):7 JUN 2006

DOI:10.1002/cjoc.200690147

Preparation of allenyl perfluoroalkyl sulfones from perfluoroalkyl sulfinyl chlorides and their reactions with secondary amines and water were studied. At room temperature secondary amines reacted readily with allenyl perfluoroalkyl sulfones to give the corresponding enamine adducts, which underwent rearrangement to afford conjugate enamines in refluxing toluene. Good diastereoslectivities were observed in the addition of diethylamine to γ-ethyl-γ-methylallenyl perfluoroalkyl sulfones. In refluxing acetonitrile, water could also undergo the similar addition with allenyl perfluoroalkyl sulfones.

Synthesis of Fluoroalkylated Heterocycles via the Reaction of 3-(1-Hydropolyfluoroalkenyl)-1-oxo-2,4,1-benzoxazines with Dinucleophilic Reagents

Co-reporter:Xian-Jin Yang

Chinese Journal of Chemistry 2006 Volume 24(Issue 10) pp:

Publication Date(Web):2 OCT 2006

DOI:10.1002/cjoc.200690265

The reaction of 3-(1-hydropolyfluoroalkenyl)-1-oxo-2,4,1-benzoxazines 1 with some dinucleophiles was investigated. 7-Fluoroalkyl-2,3-dihydro-1,4-diazepine[1,2-d]quinazolin-11-ones 2, 2-fluoroalkylisoxazolo[3,2-b]quin-azolin-9-ones 3 and 2-fluoroalkylbenzoimidazoles 4 were obtained from the reaction of 1 with 1,2-diaminoethane, hydroxylamine hydrochloride and 1,2-diaminobenzene respectively.

Synthesis of 5-fluoroalkyl lsoxazolidines via 1,3-dipolar cycloaddition of ethyl 2-hydropolyfluoroalk-2-enoates with nitrones

Co-reporter:Jin-Tao Liu;Qi-Hui Jin;He-Jun Lü;Wei-Yuan Huang

Chinese Journal of Chemistry 2004 Volume 22(Issue 9) pp:

Publication Date(Web):26 AUG 2010

DOI:10.1002/cjoc.20040220914

1,3-Dipolar cycloaddition reactions of ethyl 2-hydropolyfluoroalk-2-enoates (1) with some nitrones were described. The reaction of 3,4-dihydroisoquinoline N-oxide (2) with 1 took place readily in methylene chloride at room temperature to give the corresponding 5-fluoroalkylisoxazolidines regioselectively as a mixture of two diastereoisomers (trans and cis) in high yields, while longer reaction time and higher temperature were needed in the case of non-cyclic nitrones. Under similar conditions the reaction of quinoline N-oxide (14) with 1 did not give the expected adducts and a ring-opening product was obtained.

Asymmetric synthesis of either diastereomer of trifluoromethylated allylic amines by the selective reduction of trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketoimines

Co-reporter:Zhen-Jiang Liu and Jin-Tao Liu

Chemical Communications 2008(Issue 41) pp:NaN5235-5235

Publication Date(Web):2008/09/12

DOI:10.1039/B810459J

Per(poly)fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction

Co-reporter:Peng Li, Li-Juan Liu and Jin-Tao Liu

Organic & Biomolecular Chemistry 2011 - vol. 9(Issue 1) pp:NaN77-77

Publication Date(Web):2010/11/17

DOI:10.1039/C0OB00699H