Literature DB >> 28077882

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

Yumei Xiao1, Hongchao Guo1, Ohyun Kwon2.   

Abstract

Recent advances in chiral-phosphine-catalyzed asymmetric annulation reactions; including annulations of allenes, alkynes, Morita-Baylis-Hillman (MBH) carbonates, and ketenes; and their applications in the synthesis of bioactive molecules and natural products are reviewed.

Entities:  

Keywords:  annulation; asymmetric catalysis; chiral phosphines; cyclization; organocatalysis

Year:  2016        PMID： 28077882      PMCID： PMC5222341     

Source DB:  PubMed          Journal:  Aldrichimica Acta        ISSN： 0002-5100            Impact factor:   3.667


  73 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.  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

3.  Josiphos-catalyzed asymmetric homodimerization of ketoketenes.

Authors:  Ahmad A Ibrahim; Pei-Hsun Wei; Gero D Harzmann; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2010-10-29       Impact factor: 4.354

4.  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

5.  Aplexone targets the HMG-CoA reductase pathway and differentially regulates arteriovenous angiogenesis.

Authors:  Jayoung Choi; Kevin Mouillesseaux; Zhiming Wang; Hannah D G Fiji; Sape S Kinderman; Georg W Otto; Robert Geisler; Ohyun Kwon; Jau-Nian Chen
Journal:  Development       Date:  2011-02-09       Impact factor: 6.868

6.  Asymmetric organocatalysis in fullerenes chemistry: enantioselective phosphine-catalyzed cycloaddition of allenoates onto C60.

Authors:  Juan Marco-Martínez; Vanesa Marcos; Silvia Reboredo; Salvatore Filippone; Nazario Martín
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-11       Impact factor: 15.336

7.  Asymmetric [3+2] cycloadditions of allenoates and dual activated olefins catalyzed by simple bifunctional N-acyl aminophosphines.

Authors:  Hua Xiao; Zhuo Chai; Chang-Wu Zheng; Ying-Quan Yang; Wen Liu; Jun-Kang Zhang; Gang Zhao
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-14       Impact factor: 15.336

8.  Asymmetric construction of functionalized bicyclic imides via [3 + 2] annulation of MBH carbonates catalyzed by dipeptide-based phosphines.

Authors:  Fangrui Zhong; Guo-Ying Chen; Xiaoyu Han; Weijun Yao; Yixin Lu
Journal:  Org Lett       Date:  2012-07-12       Impact factor: 6.005

9.  Catalytic crossed Michael cycloisomerization of thioenoates: total synthesis of (+/-)-ricciocarpin A.

Authors:  Kyriacos Agapiou; Michael J Krische
Journal:  Org Lett       Date:  2003-05-15       Impact factor: 6.005

10.  Catalytic asymmetric [4+2] annulation initiated by an aza-Rauhut-Currier reaction: facile entry to highly functionalized tetrahydropyridines.

Authors:  Zugui Shi; Peiyuan Yu; Teck-Peng Loh; Guofu Zhong
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-02       Impact factor: 15.336
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  9 in total

Review 1.  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

2.  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

3.  Enantioselective Coupling of Dienes and Phosphine Oxides.

Authors:  Shao-Zhen Nie; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-11-19       Impact factor: 15.419

4.  Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines: a facile synthesis of tetrahydropyridines.

Authors:  Leijie Zhou; Chunhao Yuan; Yuan Zeng; Honglei Liu; Chang Wang; Xing Gao; Qijun Wang; Cheng Zhang; Hongchao Guo
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

Review 5.  Organophosphine-Catalyzed [4C+X] Annulations.

Authors:  Yangyan Li; Xiang Chen; Xiaoming Chen; Xiao Shen
Journal:  Molecules       Date:  2018-11-19       Impact factor: 4.411

6.  Phosphine-Promoted [4 + 3] Annulation of Allenoate with Aziridines for Synthesis of Tetrahydroazepines: Phosphine-Dependent [3 + 3] and [4 + 3] Pathways.

Authors:  Honglei Liu; Yan Lin; Yan Zhao; Miaoren Xiao; Leijie Zhou; Qijun Wang; Cheng Zhang; Dongqi Wang; Ohyun Kwon; Hongchao Guo
Journal:  RSC Adv       Date:  2019-01-09       Impact factor: 4.036

7.  Catalyst-free hydrophosphination of alkenes in presence of 2-methyltetrahydrofuran: a green and easy access to a wide range of tertiary phosphines.

Authors:  Damien Bissessar; Julien Egly; Thierry Achard; Pascal Steffanut; Stéphane Bellemin-Laponnaz
Journal:  RSC Adv       Date:  2019-08-30       Impact factor: 3.361

8.  Catalytic Enantioselective Synthesis of Guvacine Derivatives through [4 + 2] Annulations of Imines with α-Methylallenoates.

Authors:  Qihai Xu; Nathan J Dupper; Andrew J Smaligo; Yi Chiao Fan; Lingchao Cai; Zhiming Wang; Adam D Langenbacher; Jau-Nian Chen; Ohyun Kwon
Journal:  Org Lett       Date:  2018-09-24       Impact factor: 6.072

9.  Enantioselective synthesis of P-chiral tertiary phosphine oxides with an ethynyl group via Cu(i)-catalyzed azide-alkyne cycloaddition.

Authors:  Ren-Yi Zhu; Long Chen; Xiao-Si Hu; Feng Zhou; Jian Zhou
Journal:  Chem Sci       Date:  2019-11-06       Impact factor: 9.825
  9 in total

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