Literature DB >> 16268617

Asymmetric transfer hydrogenation of ketones catalyzed by hydrophobic metal-amido complexes in aqueous micelles and vesicles.

Fei Wang1, Hui Liu, Linfeng Cun, Jin Zhu, Jingen Deng, Yaozhong Jiang.   

Abstract

[Reaction: see text]. Asymmetric transfer hydrogenation of ketones, especially alpha-bromomethyl aromatic ketones, catalyzed by unmodified, hydrophobic transition metal-amido complexes (TsDPEN-M), was performed successfully with significant enhancement of activity, chemoselectivity, and enantioselectivity (up to 99% ee) in aqueous media containing micelles and vesicles. The hydrophobic catalyst, embedded in micelles constructed from the surfactant cetyltrimethylammonium bromide (CTAB), could be separated from the organic phase along with the products and was recycled for at least six times.

Entities:  

Year:  2005        PMID: 16268617     DOI: 10.1021/jo0514826

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

1.  Solubilization of Hydrophobic Catalysts Using Nanoparticle Hosts.

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Journal:  Small       Date:  2017-12-22       Impact factor: 13.281

2.  Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols.

Authors:  Kun Huang; Haiyang Wang; Viatcheslav Stepanenko; Melvin De Jesús; Carilyn Torruellas; Wildeliz Correa; Margarita Ortiz-Marciales
Journal:  J Org Chem       Date:  2011-02-04       Impact factor: 4.354

3.  De Novo Asymmetric Syntheses of d-, l- and 8-epi-Swainsonine.

Authors:  Haibing Guo; George A O'Doherty
Journal:  Tetrahedron       Date:  2008-01-07       Impact factor: 2.457

4.  Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.

Authors:  Hai-Yang Wang; Kun Huang; Melvin De Jesús; Sandraliz Espinosa; Luis E Piñero-Santiago; Charles L Barnes; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2016-02-15

Review 5.  Opportunities offered by chiral η⁶-arene/N-arylsulfonyl-diamine-RuII catalysts in the asymmetric transfer hydrogenation of ketones and imines.

Authors:  Jiří Václavík; Petr Kačer; Marek Kuzma; Libor Cervený
Journal:  Molecules       Date:  2011-06-28       Impact factor: 4.411

6.  Highly enantioselective production of (R)-halohydrins with whole cells of Rhodotorula rubra KCh 82 culture.

Authors:  Tomasz Janeczko; Monika Dymarska; Edyta Kostrzewa-Susłow
Journal:  Int J Mol Sci       Date:  2014-12-04       Impact factor: 5.923

7.  Synthesis, Absolute Configuration, Antibacterial, and Antifungal Activities of Novel Benzofuryl β-Amino Alcohols.

Authors:  Agnieszka Tafelska-Kaczmarek; Renata Kołodziejska; Marcin Kwit; Bartosz Stasiak; Magdalena Wypij; Patrycja Golińska
Journal:  Materials (Basel)       Date:  2020-09-14       Impact factor: 3.623

  7 in total

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