Zhongwen Wang

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Name: 王忠文; ZhongWen Wang

Organization: Nankai University , China

Department: State Key Laboratory and Institute of Elemento-Organic Chemistry

Title: Professor(PhD)

TOPICS

Organic Chemistry

C-H Activation

Chemicals
References

Sc(OTf)3-Catalyzed Diastereoselective Formal [3+2] Cycloaddition Reactions of Alkynylcyclopropane Ketones with Electron-Rich Aromatic Aldehydes To Yield 2,5-trans-Tetrahydrofurans

Co-reporter:Chi Zhang;Muyun Xu;Jun Ren

European Journal of Organic Chemistry 2016 Volume 2016( Issue 14) pp:2467-2478

Publication Date(Web):

DOI:10.1002/ejoc.201600233

Abstract

In contast to the general [4+2] cycloaddition reactions of alkynylcyclopropane ketones reported in the literature, we report herein a Sc(OTf)₃-catalyzed formal intermolecular [3+2] cycloaddition reaction of alkynylcyclopropane ketones with electron-rich aromatic aldehydes. 2,3,3,5-Tetrasubstituted tetrahydrofurans were obtained by this method, and the tetrahydrofuran skeleton was diastereoselectively constructed with a 2,5-trans configuration. This is also quite different to the 2,5-cis configuration usually obtained from typical [3+2] cycloaddition reactions of most donor–acceptor cyclopropanes. Additionally, the cycloadducts were subjected to a domino carbopalladation/C–H activation/C–C bond-formation process for the highly efficient construction of polycyclic skeletons.

Lewis Acid Catalyzed Intramolecular [3 + 2] Cross Cycloadditions of Cobalt-Alkynylcyclopropane 1,1-Diesters with Carbonyls for Construction of Medium-Sized and Polycyclic Skeletons

Co-reporter:Junhui Zhang, Siyang Xing, Jun Ren, Shende Jiang, and Zhongwen Wang

Organic Letters 2015 Volume 17(Issue 2) pp:218-221

Publication Date(Web):December 23, 2014

DOI:10.1021/ol503285u

A Lewis acid catalyzed intramolecular [3 + 2] cross cycloaddition of cobalt-alkynylcyclopropane 1,1-diesters with carbonyls has been successfully developed. Together with simple and efficient postcycloadditions of the cobalt-alkyne moiety, a general and efficient strategy for construction of structurally complex and diverse medium-sized skeletons and related polycycles was supplied successfully.

Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons

Co-reporter:Weiwei Ma, Jie Fang, Jun Ren, and Zhongwen Wang

Organic Letters 2015 Volume 17(Issue 17) pp:4180-4183

Publication Date(Web):August 27, 2015

DOI:10.1021/acs.orglett.5b01927

A novel Lewis acid catalyzed formal intramolecular [3 + 3] cross-cycloaddition (IMCC) of cyclopropane 1,1-diesters has been successfully developed. This supplies an efficient and conceptually new strategy for construction of bridged bicyclo[2.2.2]octane skeletons. This [3 + 3]IMCC could be run up to gram scale and from easily prepared starting materials. This [3 + 3]IMCC, together with our previously reported [3 + 2]IMCC strategy, can afford either the bicyclo[2.2.2]octane or bicyclo[3.2.1]octane skeletons from the similar starting materials by regulating the substituents on vinyl group.

Cooperative Photo-/Lewis Acid Catalyzed Tandem Intramolecular [3 + 2] Cross-Cycloadditions of Cyclopropane 1,1-Diesters with α,β-Unsaturated Carbonyls for Medium-Sized Carbocycles

Co-reporter:Zhenjun Wang, Shuai Chen, Jun Ren, and Zhongwen Wang

Organic Letters 2015 Volume 17(Issue 17) pp:4184-4187

Publication Date(Web):August 27, 2015

DOI:10.1021/acs.orglett.5b01928

A tandem isomerization/intramolecular [3 + 2] cross-cycloaddition (IMCC) of cyclopropane 1,1-diesters with α,β-unsaturated ketones/aldehydes under a cooperative catalysis of photo and Lewis acids has been successfully developed. This supplied a general and efficient strategy for construction of medium-sized carbocyclic (8-, 9-, and 10-membered) skeletons as well as such carbocycle-based bridged oxa-bicyclo[n.2.1] (n = 4–6) skeletons.

Acid-Catalyzed Domino Meinwald Rearrangement of Epoxides/Intramolecular [3+2] Cross-Cycloaddition of Cyclopropane-1,1-dicarboxylates

Co-reporter:Wenju Zhu;Jun Ren

European Journal of Organic Chemistry 2014 Volume 2014( Issue 17) pp:3561-3564

Publication Date(Web):

DOI:10.1002/ejoc.201402160

Abstract

An acid-catalyzed domino Meinwald rearrangement of epoxides/intramolecular [3+2] cross-cycloaddition of cyclopropane 1,1-diesters was developed. This supplied a method for the construction of bridged oxa-[n.2.1] (n = 3, 4) skeletons.

An unexpected Lewis acids-catalyzed tandem ring-opening rearrangement of vinylcyclopropane ketone with aryl aldehyde

Co-reporter:Jun Ren, Yu Bai, Weijie Tao, Zhongwen Wang

Tetrahedron Letters 2014 Volume 55(Issue 15) pp:2545-2547

Publication Date(Web):9 April 2014

DOI:10.1016/j.tetlet.2014.03.035

A novel tandem reaction of vinylcyclopropane ketone with benzaldehyde has been successfully developed. This provides a new method for the preparation of γ-oxo-hexenone derivatives from easily accessible starting materials.

TfOH-Catalyzed Formal [3 + 2] Cycloaddition of Cyclopropane 1,1-Diesters with Nitriles

Co-reporter:Bo Cui, Jun Ren, and Zhongwen Wang

The Journal of Organic Chemistry 2014 Volume 79(Issue 2) pp:790-796

Publication Date(Web):December 13, 2013

DOI:10.1021/jo402383a

A triflic acid-catalyzed formal [3 + 2] cycloaddition of cyclopropane 1,1-diesters with nitriles was developed. This reaction was expeditious, and the scope of the substituents in both cyclopropanes and nitriles was broad. This supplies an efficient and practical method for the synthesis of 1-pyrrolines.

Lewis Acids Promoted Formal Intramolecular [3 + 2] Parallel and Cross-Cycloadditions of Cyclopropane 1,1-Diesters with Allenes

Co-reporter:Zhenjun Wang, Jun Ren, and Zhongwen Wang

Organic Letters 2013 Volume 15(Issue 22) pp:5682-5685

Publication Date(Web):October 30, 2013

DOI:10.1021/ol402662j

A novel Lewis acid promoted formal intramolecular [3 + 2] parallel/cross-cycloaddition of cyclopropane 1,1-diesters with allenes has been successfully developed, in which the two C═C of allenes were involved respectively. This provides a general and efficient strategy for the construction of structurally diverse [4.3.0]nonane and [3.2.1]octane skeletons.

Synthesis of Substituted Furans through Domino Aldol/Homo-Michael Reactions of Formylcyclopropane 1,1-Diesters with 1,3-Dicarbonyls

Co-reporter:Jilai Bao;Jun Ren

European Journal of Organic Chemistry 2012 Volume 2012( Issue 13) pp:2511-2515

Publication Date(Web):

DOI:10.1002/ejoc.201200162

Abstract

A Lewis acid catalyzed domino aldol/homo-Michael reaction of formylcyclopropane 1,1-diesters with dicarbonyls has been successfully developed. This method provides efficient and direct construction of highly functionalized furans from easily available starting materials.

Lewis Acid Catalyzed Intramolecular [4+2] and [3+2] Cross-Cycloaddition of Alkynylcyclopropane Ketones with Carbonyl Compounds and Imines

Co-reporter:Dr. Yu Bai;Weijie Tao;Jun Ren ; Zhongwen Wang

Angewandte Chemie 2012 Volume 124( Issue 17) pp:4188-4192

Publication Date(Web):

DOI:10.1002/ange.201200450

Lewis Acid Catalyzed Intramolecular [4+2] and [3+2] Cross-Cycloaddition of Alkynylcyclopropane Ketones with Carbonyl Compounds and Imines

Co-reporter:Dr. Yu Bai;Weijie Tao;Jun Ren ; Zhongwen Wang

Angewandte Chemie International Edition 2012 Volume 51( Issue 17) pp:4112-4116

Publication Date(Web):

DOI:10.1002/anie.201200450

N-Heterocyclic Carbene Catalyzed Domino Reactions of Formylcyclopropane 1,1-Diesters: Construction of a 6-5-5 Tricyclic Pyrrolo[1,2-a]indole

Co-reporter:Linxia Li;Ding Du;Jun Ren

European Journal of Organic Chemistry 2011 Volume 2011( Issue 3) pp:614-618

Publication Date(Web):

DOI:10.1002/ejoc.201001364

Abstract

Catalyzed by N-heterocyclic carbenes (NHCs), a domino ring-opening/redox amidation/Knoevenagel condensation of readily available formylcyclopropane 1,1-diesters with 1H-indole-2-carbaldehydes is reported. This methodology provides a new and direct method for the construction of a 6-5-5 tricyclic pyrrolo[1,2-a]indole skeleton.

Lewis acid-catalyzed nucleophilic ring-opening/intramolecular Conia-ene reactions of methylenecyclopropane 1,1-diesters with propargyl alcohols

Co-reporter:Bao Hu, Jun Ren, Zhongwen Wang

Tetrahedron 2011 67(4) pp: 763-768

Publication Date(Web):

DOI:10.1016/j.tet.2010.11.048

Lewis Acid Catalyzed Intramolecular [3+2] Cross-Cycloaddition of DonorAcceptor Cyclopropanes with Carbonyls: A General Strategy for the Construction of Acetal[n.2.1] Skeletons

Co-reporter:Dr. Siyang Xing;Yan Li;Zhen Li;Chang Liu;Jun Ren ; Zhongwen Wang

Angewandte Chemie International Edition 2011 Volume 50( Issue 52) pp:12605-12609

Publication Date(Web):

DOI:10.1002/anie.201106368

Lewis Acid Catalyzed Intramolecular [3+2] Cross-Cycloaddition of DonorAcceptor Cyclopropanes with Carbonyls: A General Strategy for the Construction of Acetal[n.2.1] Skeletons

Co-reporter:Dr. Siyang Xing;Yan Li;Zhen Li;Chang Liu;Jun Ren ; Zhongwen Wang

Angewandte Chemie 2011 Volume 123( Issue 52) pp:12813-12817

Publication Date(Web):

DOI:10.1002/ange.201106368

A nBuLi-Mediated, Expeditious and Stereoselective Ring-Opening Rearrangement of (Arylmethylene)cyclopropane-1,1-dicarboxylates

Co-reporter:Bao Hu;Linan Jiang;Jun Ren

European Journal of Organic Chemistry 2010 Volume 2010( Issue 7) pp:1358-1363

Publication Date(Web):

DOI:10.1002/ejoc.200901165

Abstract

We report herein an nBuLi-mediated, expeditious, ring-opening rearrangement of (arylmethylene)cyclopropane 1,1-diesters to prepare 1,3-diene derivatives with good stereoselectivity. The reaction mechanism has also been discussed.

Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1,1-diester

Co-reporter:Bao Hu, Siyang Xing, Jun Ren, Zhongwen Wang

Tetrahedron 2010 66(30) pp: 5671-5674

Publication Date(Web):

DOI:10.1016/j.tet.2010.05.057

Efficient Construction of Oxa- and Aza-[n.2.1] Skeletons: Lewis Acid Catalyzed Intramolecular [3+2]Cycloaddition of Cyclopropane 1,1-Diesters with Carbonyls and Imines

Co-reporter:Siyang Xing Dr.;Wenyan Pan;Chang Liu;Jun Ren

Angewandte Chemie 2010 Volume 122( Issue 18) pp:3283-3286

Publication Date(Web):

DOI:10.1002/ange.201000563

Efficient Construction of Oxa- and Aza-[n.2.1] Skeletons: Lewis Acid Catalyzed Intramolecular [3+2]Cycloaddition of Cyclopropane 1,1-Diesters with Carbonyls and Imines

Co-reporter:Siyang Xing Dr.;Wenyan Pan;Chang Liu;Jun Ren

Angewandte Chemie International Edition 2010 Volume 49( Issue 18) pp:3215-3218

Publication Date(Web):

DOI:10.1002/anie.201000563

N-Heterocyclic Carbene-Catalyzed Domino Ring-Opening/Redox Amidation/Cyclization Reactions of Formylcyclopropane 1,1-Diesters: Direct Construction of a 6−5−6 Tricyclic Hydropyrido[1,2-a]indole Skeleton

Co-reporter:Ding Du, Linxia Li and Zhongwen Wang

The Journal of Organic Chemistry 2009 Volume 74(Issue 11) pp:4379-4382

Publication Date(Web):May 7, 2009

DOI:10.1021/jo900650h

Catalyzed by N-heterocyclic carbenes (NHCs), domino ring-opening/redox amidation/cyclization reactions of the readily available formylcyclopropane 1,1-diesters with 2-chloro-1H-indole-3-carboaldehydes were reported. This methodology provides an efficient and direct construction of a 6−5−6 tricyclic hydropyrido[1,2-a]indole skeleton, which can be potentially applied for the synthesis of several types of polycyclic indole alkaloids.

A highly regioselective tandem 1,3-dipolar cycloaddition of cyclopropene 1,1-diesters and nitrile oxides: synthesis of highly functionalized isoxazoles

Co-reporter:Shaojin Chen, Jun Ren, Zhongwen Wang

Tetrahedron 2009 65(45) pp: 9146-9151

Publication Date(Web):

DOI:10.1016/j.tet.2009.09.034

Highly Diastereoselective Gold- or Copper-Catalyzed Formal [4+3] Cycloaddition of 1-(1-Alkynyl) Cyclopropyl Ketones and Nitrones

Co-reporter:Yu Bai;Jie Fang;Jun Ren Dr.

Chemistry - A European Journal 2009 Volume 15( Issue 36) pp:8975-8978

Publication Date(Web):

DOI:10.1002/chem.200901133

A Highly Site-, Regio-, and Stereoselective Lewis Acid Catalyzed Formal [3+3] Cycloaddition of Methylenecyclopropane-1,1-Diesters with C,N-Diarylnitrones

Co-reporter:Bao Hu Dr.;Jianlin Zhu;Siyang Xing;Jie Fang;Ding Du

Chemistry - A European Journal 2009 Volume 15( Issue 2) pp:324-327

Publication Date(Web):

DOI:10.1002/chem.200801990

A modified total synthesis of cystothiazole A

Co-reporter:YueXia Bai;JiLai Bao;Jun Ren

Science China Chemistry 2009 Volume 52( Issue 9) pp:1345-1352

Publication Date(Web):2009 September

DOI:10.1007/s11426-009-0185-x

A modified total synthesis of cystothiazole A is described. In this synthetic strategy, a one-step transformation of acylated oxazolidinone to β-ketoester has been successfully applied, thus making the synthetic route more efficient. This method may also be potentially applied in synthesis of other related β-substituted-β-methoxyl acrylates (bb-MOAs).

N-Heterocyclic Carbene-Catalyzed Domino Reactions of Formylcyclopropane 1,1-Diesters: A New Synthesis of Coumarins

Co-reporter:Ding Du

European Journal of Organic Chemistry 2008 Volume 2008( Issue 29) pp:4949-4954

Publication Date(Web):

DOI:10.1002/ejoc.200800599

Abstract

N-Heterocyclic carbenes (NHCs) catalyze the reaction of formylcyclopropane 1,1-diesters with salicylaldehydes in a domino redox esterification/cyclization reaction to give coumarins in moderate to excellent yields. In addition, we also report the intramolecular conversion of compound 2f to dihydropyranone 4 catalyzed by NHC D. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)