Literature DB >> 19374356

Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: facile entry into highly functionalized tetrahydropyridines.

Hongchao Guo1, Qihai Xu, Ohyun Kwon.   

Abstract

The phosphine-mediated [3 + 3] annulations of aziridines and allenes are experimentally simple reactions, run under very mild conditions, for the preparation of highly functionalized tetrahydropyridines in yields of up to 98% and trans/cis ratios of up to 97:3. In addition to steps that are typical of nucleophilic phosphine-catalyzed reactions of allenoates, the mechanism of this new reaction features apparent nucleophilic aromatic substitution and concomitant desulfonylation, processes hitherto unknown during phosphine-promoted cycloaddition reactions. Notably, these reactions are the first reported examples of aziridines as reaction partners in nucleophilic phosphine-catalyzed transformations.

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Year:  2009        PMID： 19374356      PMCID： PMC2749062          DOI： 10.1021/ja8097349

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  26 in total

1.  Intramolecular organocatalytic [3+2] dipolar cycloaddition: stereospecific cycloaddition and the total synthesis of (+/-)-hirsutene.

Authors:  Jian-Cheng Wang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2003       Impact factor: 15.336

2.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors:  Paul Müller; Corinne Fruit
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  An unexpected role of a trace amount of water in catalyzing proton transfer in phosphine-catalyzed (3 + 2) cycloaddition of allenoates and alkenes.

Authors:  Yuanzhi Xia; Yong Liang; Yuanyuan Chen; Ming Wang; Lei Jiao; Feng Huang; Song Liu; Yahong Li; Zhi-Xiang Yu
Journal:  J Am Chem Soc       Date:  2007-02-24       Impact factor: 15.419

4.  Palladium-catalyzed asymmetric [3+3] cycloaddition of trimethylenemethane derivatives with nitrones.

Authors:  Ryo Shintani; Soyoung Park; Wei-Liang Duan; Tamio Hayashi
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Phosphine-catalyzed [4 + 2] annulation: synthesis of cyclohexenes.

Authors:  Yang S Tran; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2007-10-03       Impact factor: 15.419

6.  Advances in nitrogen transfer reactions involving aziridines.

Authors:  Iain D G Watson; Lily Yu; Andrei K Yudin
Journal:  Acc Chem Res       Date:  2006-03       Impact factor: 22.384

Review 7.  Synthesis and reactivity of C-heteroatom-substituted aziridines.

Authors:  Girija S Singh; Matthias D'hooghe; Norbert De Kimpe
Journal:  Chem Rev       Date:  2007-05       Impact factor: 60.622

8.  Stereoselective intermolecular formal [3+3] cycloaddition reaction of cyclic enamines and enones.

Authors:  Mohammad Movassaghi; Bin Chen
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

9.  Reactions of electron-deficient alkynes and allenes under phosphine catalysis.

Authors:  X Lu; C Zhang; Z Xu
Journal:  Acc Chem Res       Date:  2001-07       Impact factor: 22.384

10.  An expedient phosphine-catalyzed [4 + 2] annulation: synthesis of highly functionalized tetrahydropyridines.

Authors:  Xue-Feng Zhu; Jie Lan; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2003-04-23       Impact factor: 15.419
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  23 in total

1.  Phosphine-initiated general base catalysis: facile access to benzannulated 1,3-diheteroatom five-membered rings via double-Michael reactions of allenes.

Authors:  Judy Szeto; Vardhineedi Sriramurthy; Ohyun Kwon
Journal:  Org Lett       Date:  2011-09-20       Impact factor: 6.005

2.  Phosphine-catalyzed β'-umpolung addition of nucleophiles to activated α-alkyl allenes.

Authors:  Tioga J Martin; Venus G Vakhshori; Yang S Tran; Ohyun Kwon
Journal:  Org Lett       Date:  2011-04-14       Impact factor: 6.005

3.  Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] pathways.

Authors:  Risong Na; Chengfeng Jing; Qihai Xu; Hui Jiang; Xi Wu; Jiayan Shi; Jiangchun Zhong; Min Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; Hongchao Guo; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2011-08-03       Impact factor: 15.419

4.  Stereoselective Syntheses of α,β-Unsaturated γ-Amino Esters Through Phosphine-Catalyzed γ-Umpolung Additions of Sulfonamides to γ-Substituted Allenoates.

Authors:  Qing-Fa Zhou; Kui Zhang; Ohyun Kwon
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

5.  Phosphine-catalyzed [4+2] annulations of 2-alkylallenoates and olefins: synthesis of multisubstituted cyclohexenes.

Authors:  Yang S Tran; Tioga J Martin; Ohyun Kwon
Journal:  Chem Asian J       Date:  2011-07-07

Review 6.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

7.  Copper-catalyzed synthesis of 2,4-disubstituted allenoates from α-diazoesters.

Authors:  Matthew Hassink; Xiaozhong Liu; Joseph M Fox
Journal:  Org Lett       Date:  2011-04-12       Impact factor: 6.005

8.  Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates.

Authors:  Chengfeng Jing; Risong Na; Bo Wang; Honglei Liu; Lei Zhang; Jun Liu; Min Wang; Jiangchun Zhong; Ohyun Kwon; Hongchao Guo
Journal:  Adv Synth Catal       Date:  2012-04-26       Impact factor: 5.837

9.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

10.  PHOSPHINE-CATALYZED [3 + 2] ANNULATION: SYNTHESIS OF ETHYL 5-(tert-BUTYL)-2-PHENYL-1-TOSYL-3-PYRROLINE-3-CARBOXYLATE.

Authors:  Ian P Andrews; Ohyun Kwon
Journal:  Organic Synth       Date:  2012
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