Literature DB >> 10814429

Unusual

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Abstract

All-carbon 1,3-dipoles derived from allenic esters/ketones, by catalytic interaction with triphenylphosphine, undergo an unusual [8 + 2] annelation with tropone, leading to 8-oxa-9-(ethoxycarbonyl/acylalkylidene)bicyclo[5.3.0]deca-1,3,5-trienes. Dipoles derived from allenic ketones as well as an alpha-methyl-substituted allenic ester display high reactivity and selectivity.

Entities:  

Year:  2000        PMID： 10814429     DOI： 10.1021/ol000007l

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 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 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

3.  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 4.  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

5.  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

6.  Theory-Guided Design of Brønsted Acid-Assisted Phosphine Catalysis: Synthesis of Dihydropyrones from Aldehydes and Allenoates.

Authors:  Gardner S Creech; Xue-Feng Zhu; Branden Fonovic; Travis Dudding; Ohyun Kwon
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

7.  Lewis acid catalyzed inverse-electron-demand Diels-Alder reaction of tropones.

Authors:  Pingfan Li; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

8.  Alcohol-assisted phosphine catalysis: one-step syntheses of dihydropyrones from aldehydes and allenoates.

Authors:  Gardner S Creech; Ohyun Kwon
Journal:  Org Lett       Date:  2008-01-04       Impact factor: 6.005

Review 9.  Phosphine catalysis of allenes with electrophiles.

Authors:  Zhiming Wang; Xingzhu Xu; Ohyun Kwon
Journal:  Chem Soc Rev       Date:  2014-03-24       Impact factor: 54.564

10.  Ni(NHC)]-catalyzed cycloaddition of diynes and tropone: apparent enone cycloaddition involving an 8π insertion.

Authors:  Puneet Kumar; Ashish Thakur; Xin Hong; K N Houk; Janis Louie
Journal:  J Am Chem Soc       Date:  2014-12-05       Impact factor: 15.419
  10 in total

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