Literature DB >> 17217278

Asymmetric hydrogenation of alpha-chloro aromatic ketones catalyzed by eta6-arene/TsDPEN-ruthenium(II) complexes.

Takeshi Ohkuma1, Kunihiko Tsutsumi, Noriyuki Utsumi, Noriyoshi Arai, Ryoji Noyori, Kunihiko Murata.   

Abstract

Asymmetric hydrogenation of various alpha-chloro aromatic ketones with Ru(OTf)(TsDPEN)(eta6-arene) (TsDPEN = N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine) produces the chiral chlorohydrins in up to 98% ee. This reaction can be conducted even on a 206-g scale. The hydrogenation of an alpha-chloro ketone with a phenol moiety has been utilized for the synthesis of (R)-norphenylephrine without protection-deprotection operations. [reaction: see text].

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Year:  2007        PMID： 17217278     DOI： 10.1021/ol062661s

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Design, synthesis, and X-ray studies of potent HIV-1 protease inhibitors incorporating aminothiochromane and aminotetrahydronaphthalene carboxamide derivatives as the P2 ligands.

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Journal:  Eur J Med Chem       Date:  2018-09-18       Impact factor: 6.514

Review 2.  Asymmetric hydrogenation of ketones: tactics to achieve high reactivity, enantioselectivity, and wide scope.

Authors:  Takeshi Ohkuma
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2010       Impact factor: 3.493

3.  Direct formation of tethered Ru(II) catalysts using arene exchange.

Authors:  Rina Soni; Katherine E Jolley; Guy J Clarkson; Martin Wills
Journal:  Org Lett       Date:  2013-09-26       Impact factor: 6.005

4.  Enantio-relay catalysis constructs chiral biaryl alcohols over cascade Suzuki cross-coupling-asymmetric transfer hydrogenation.

Authors:  Dacheng Zhang; Xiaoshuang Gao; Tanyu Cheng; Guohua Liu
Journal:  Sci Rep       Date:  2014-05-28       Impact factor: 4.379

5.  pH-Dependent transfer hydrogenation or dihydrogen release catalyzed by a [(η6-arene)RuCl(κ2-N,N-dmobpy)]+ complex: a DFT mechanistic understanding.

Authors:  Chenguang Luo; Longfei Li; Xin Yue; Pengjie Li; Lin Zhang; Zuoyin Yang; Min Pu; Zexing Cao; Ming Lei
Journal:  RSC Adv       Date:  2020-03-11       Impact factor: 4.036

6.  One-pot synthesis of chiral alcohols from alkynes by CF3SO3H/ruthenium tandem catalysis.

Authors:  Huan Liu; Sensheng Liu; Haifeng Zhou; Qixing Liu; Chunqin Wang
Journal:  RSC Adv       Date:  2018-04-19       Impact factor: 4.036

7.  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

8.  Boron Tetrafluoride Anion Bonding Dual Active Species Within a Large-Pore Mesoporous Silica for Two-Step Successive Organic Transformaion to Prepare Optically Pure Amino Alcohols.

Authors:  Liang Li; Dongfeng Yang; Zhongrui Zhao; Yongkang Song; Lei Zhao; Rui Liu; Guohua Liu
Journal:  Front Chem       Date:  2018-07-06       Impact factor: 5.221
  8 in total

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