Literature DB >> 21063612

Organocatalytic enantioselective desymmetrization of cyclic enones via phosphine promoted [3+2] annulations.

Nathalie Pinto1, Pascal Retailleau, Arnaud Voituriez, Angela Marinetti.   

Abstract

Phosphine catalyzed enantioselective [3+2] cyclizations on 4-substituted 2,6-diarylidenecyclohexanones and 2,4-diarylidene-bicyclo[3.1.0]hexan-3-ones take place with high diastereo- and enantioselectivity levels. The process affords spirocyclic compounds with excellent stereochemical control of up to five stereogenic centres.

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Year:  2010        PMID： 21063612     DOI： 10.1039/c0cc03164j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  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.  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

3.  Application of a new chiral phosphepine to the catalytic asymmetric synthesis of highly functionalized cyclopentenes that bear an array of heteroatom-substituted quaternary stereocenters.

Authors:  Yuji Fujiwara; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2011-07-18       Impact factor: 15.419

4.  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

5.  Enantioselective one-pot synthesis of α-amino esters by a phosphine-catalyzed [3+2]-cycloaddition reaction.

Authors:  Marianne Steurer; Kim L Jensen; Dennis Worgull; Karl Anker Jørgensen
Journal:  Chemistry       Date:  2011-12-07       Impact factor: 5.236

6.  Design, synthesis and application of a new type of bifunctional Le-Phos in highly enantioselective γ-addition reactions of N-centered nucleophiles to allenoates.

Authors:  Haile Qiu; Xiaofeng Chen; Junliang Zhang
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

7.  [3+2] regioselective annulation reaction of 2-arylidene-1,3-indandiones towards synthesis of spirocyclopentenes: understanding the mechanism of γ-attack vs. α-attack using DFT studies.

Authors:  Shaik Anwar; Li-Tzu Lin; V Srinivasadesikan; Veera Babu Gudise; Kwunmin Chen
Journal:  RSC Adv       Date:  2021-12-01       Impact factor: 4.036

Review 8.  Chiral phosphines in nucleophilic organocatalysis.

Authors:  Yumei Xiao; Zhanhu Sun; Hongchao Guo; Ohyun Kwon
Journal:  Beilstein J Org Chem       Date:  2014-09-04       Impact factor: 2.883

9.  Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones.

Authors:  Guo-Peng Wang; Yao-Liang Sun; Shou-Fei Zhu; Yin Wei; Qi-Lin Zhou; Min Shi
Journal:  Chem Sci       Date:  2015-09-15       Impact factor: 9.825
  9 in total

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