Literature DB >> 24663290

Phosphine catalysis of allenes with electrophiles.

Zhiming Wang1, Xingzhu Xu, Ohyun Kwon.   

Abstract

Nucleophilic phosphine catalysis of allenes with electrophiles is one of the most powerful and straightforward synthetic strategies for the generation of highly functionalized carbocycle or heterocycle structural motifs, which are present in a wide range of bioactive natural products and medicinally important substances. The reaction topologies can be controlled through a judicious choice of the phosphine catalyst and the structural variations of starting materials. This Tutorial Review presents selected examples of nucleophilic phosphine catalysis using allenes and electrophiles.

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Year:  2014        PMID： 24663290      PMCID： PMC4059616          DOI： 10.1039/c4cs00054d

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN： 0306-0012            Impact factor:   54.564


  36 in total

1.  Versatile enantioselective [3+2] cyclization between imines and allenoates catalyzed by dipeptide-based phosphines.

Authors:  Xiaoyu Han; Fangrui Zhong; Youqing Wang; Yixin Lu
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-07       Impact factor: 15.336

2.  Small-molecule inhibitors of protein geranylgeranyltransferase type I.

Authors:  Sabrina Castellano; Hannah D G Fiji; Sape S Kinderman; Masaru Watanabe; Pablo de Leon; Fuyuhiko Tamanoi; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2007-04-17       Impact factor: 15.419

3.  Diversity through a branched reaction pathway: generation of multicyclic scaffolds and identification of antimigratory agents.

Authors:  Zhiming Wang; Sabrina Castellano; Sape S Kinderman; Christian E Argueta; Anwar B Beshir; Gabriel Fenteany; Ohyun Kwon
Journal:  Chemistry       Date:  2010-11-09       Impact factor: 5.236

4.  Annulation reactions of allene-derived 1,3-dipole with 3-substituted-chromones: unusual recognition of 4pi-component in 3-(N-Aryliminomethyl)chromones through

Authors: 
Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

5.  Diversity through phosphine catalysis identifies octahydro-1,6-naphthyridin-4-ones as activators of endothelium-driven immunity.

Authors:  Daniel Cruz; Zhiming Wang; Jon Kibbie; Robert Modlin; Ohyun Kwon
Journal:  Proc Natl Acad Sci U S A       Date:  2011-03-07       Impact factor: 11.205

6.  Diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans via phosphine-catalyzed [4 + 2] annulation of α-benzylallenoates with ketones.

Authors:  Tong Wang; Song Ye
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

7.  A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol.

Authors:  Yishu Du; Xiyan Lu
Journal:  J Org Chem       Date:  2003-08-08       Impact factor: 4.354

8.  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

9.  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

10.  Total synthesis of (±)-hirsutine: application of phosphine-catalyzed imine-allene [4 + 2] annulation.

Authors:  Reymundo A Villa; Qihai Xu; Ohyun Kwon
Journal:  Org Lett       Date:  2012-08-24       Impact factor: 6.005
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  34 in total

1.  Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine-Palladium Catalysis.

Authors:  Yi Chiao Fan; Ohyun Kwon
Journal:  Org Lett       Date:  2015-04-14       Impact factor: 6.005

2.  Biphilic Organophosphorus Catalysis: Regioselective Reductive Transposition of Allylic Bromides via P(III)/P(V) Redox Cycling.

Authors:  Kyle D Reichl; Nicole L Dunn; Nicholas J Fastuca; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2015-04-21       Impact factor: 15.419

3.  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

4.  Phosphine-Mediated Iterative Arene Homologation Using Allenes.

Authors:  Kui Zhang; Lingchao Cai; Xing Jiang; Miguel A Garcia-Garibay; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2015-08-31       Impact factor: 15.419

Review 5.  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

6.  Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes.

Authors:  Qing-Fa Zhou; Kui Zhang; Lingchao Cai; Ohyun Kwon
Journal:  Org Lett       Date:  2016-05-27       Impact factor: 6.005

7.  Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.

Authors:  Yumei Xiao; Hongchao Guo; Ohyun Kwon
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

8.  Phosphine-Catalyzed α-Umpolung-Aldol Reaction for the Synthesis of Benzo[ b]azapin-3-ones.

Authors:  Kui Zhang; Lingchao Cai; Sooji Hong; Ohyun Kwon
Journal:  Org Lett       Date:  2019-06-20       Impact factor: 6.005

Review 9.  Phosphorus-Based Catalysis.

Authors:  Changmin Xie; Andrew J Smaligo; Xian-Rong Song; Ohyun Kwon
Journal:  ACS Cent Sci       Date:  2021-03-16       Impact factor: 14.553

10.  A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A.

Authors:  Chaofan Huang; Fuchun Shi; Yifan Cui; Can Li; Jie Lin; Qi Liu; Anni Qin; Huanan Wang; Guolin Wu; Penglin Wu; Junzhe Xiao; Haibo Xu; Yuan Yuan; Yizhan Zhai; Wei-Feng Zheng; Yangguangyan Zheng; Biao Yu; Shengming Ma
Journal:  Chem Sci       Date:  2021-06-09       Impact factor: 9.825
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