Literature DB >> 24976341

Phosphine-catalyzed asymmetric [4+1] annulation of activated α,β-unsaturated ketones with Morita-Baylis-Hillman carbonates: enantioselective synthesis of spirooxindoles containing two adjacent quaternary stereocenters.

Fang-Le Hu1, Yin Wei, Min Shi.   

Abstract

The asymmetric [4+1] annulation of activated α,β-unsaturated ketones with MBH carbonates catalyzed by bifunctional thiourea-phosphine catalysts derived from an axially chiral binaphthyl scaffold has been developed, giving spirooxindoles with two adjacent quaternary stereocenters in good yields with high enantioselectivities and moderate diastereoselectivities under mild conditions.

Entities:  

Year:  2014        PMID: 24976341     DOI: 10.1039/c4cc03479a

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


  6 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.  Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters.

Authors:  Chung Whan Lee; Seo-Jung Han; Scott C Virgil; Brian M Stoltz
Journal:  Tetrahedron       Date:  2015-06-03       Impact factor: 2.457

3.  An unusual stereoretentive 1,3-quaternary carbon shift resulting in an enantioselective RhII-catalyzed formal [4+1]-cycloaddition between diazo compounds and vinyl ketenes.

Authors:  Kevin X Rodriguez; Tara C Pilato; Brandon L Ashfeld
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

4.  Synthesis, crystal structure, DFT calculations and Hirshfeld surface analysis of 2-(1-decyl-2-oxo-indolin-3-yl-idene)propanedi-nitrile.

Authors:  Ibtissam Rayni; Youness El Bakri; Chin-Hung Lai; L'houssaine El Ghayati; El Mokhtar Essassi; Joel T Mague
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-01-01

5.  Phosphine-mediated enantioselective [1 + 4]-annulation of Morita-Baylis-Hillman carbonates with 2-enoylpyridines.

Authors:  Tao Wang; Pengfei Zhang; Wenjun Li; Pengfei Li
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 3.361

6.  SO2F2 mediated cascade dehydrogenative Morita-Baylis-Hillman reaction of the C(sp3)-H of primary alcohols with the C(sp2)-H of electron-deficient olefins for the assembly of allylic alcohols.

Authors:  Ying Jiang; Njud S Alharbi; Bing Sun; Hua-Li Qin
Journal:  RSC Adv       Date:  2019-09-20       Impact factor: 3.361

  6 in total

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