Literature DB >> 15728390

A remarkably effective copper(II)-dipyridylphosphine catalyst system for the asymmetric hydrosilylation of ketones in air.

Jing Wu1, Jian-Xin Ji, Albert S C Chan.   

Abstract

The combination of catalytic amounts of optically active dipyridylphosphine and CuF(2) along with hydride donor PhSiH(3) generated in situ a remarkably reactive catalyst system (substrate-to-ligand molar ratio up to 100,000) for the highly enantioselective hydrosilylation of a broad spectrum of aryl alkyl ketones (up to 97% enantiomeric excess) in normal atmosphere and at mild conditions (ambient temperature to -20 degrees C, compatible with traces of moisture) in the absence of base additives. Furthermore, a highly effective catalytic asymmetric hydrosilylation of unsymmetrical diarylketones using this catalyst system was also realized (up to 98% enantiomeric excess). The introduction of the dipyridylphosphine ligands in the air-accelerated and inexpensive metal-mediated asymmetric hydrosilylation of ketones makes the present system highly attractive and thus provides an excellent opportunity for practical applications.

Entities:  

Year:  2005        PMID: 15728390      PMCID: PMC553317          DOI: 10.1073/pnas.0409043102

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  18 in total

1.  Copper(I) hydride-catalyzed asymmetric hydrosilylation of heteroaromatic ketones.

Authors:  Bruce H Lipshutz; Asher Lower; Kevin Noson
Journal:  Org Lett       Date:  2002-11-14       Impact factor: 6.005

2.  Asymmetric hydrogenation of ketones catalyzed by RuII-bicp complexes.

Authors:  Daniel G Genov; David J Ager
Journal:  Angew Chem Int Ed Engl       Date:  2004-05-17       Impact factor: 15.336

3.  Asymmetric catalysis: science and opportunities (Nobel lecture).

Authors:  Ryoji Noyori
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-17       Impact factor: 15.336

4.  Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones.

Authors:  Ryoji Noyori; Takeshi Ohkuma
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

5.  The antihistaminic and anticholinergic activities of optically active diphenhydramine derivatives. The concept of complementarity.

Authors:  R F Rekker; H Timmerman; A F Harms; W T Nauta
Journal:  Arzneimittelforschung       Date:  1971-05

6.  The resolution in optical isomers of orphenadrine, 4-methyldiphenhydramine and their N-demethyl derivatives.

Authors:  C van der Stelt; W J Heus; W T Nauta
Journal:  Arzneimittelforschung       Date:  1969-12

7.  Selective hydrogenation of benzophenones to benzhydrols. Asymmetric synthesis of unsymmetrical diarylmethanols

Authors: 
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

8.  A modular assembly of chiral oxazolinylcarbene-rhodium complexes: efficient phosphane-free catalysts for the asymmetric hydrosilylation of dialkyl ketones.

Authors:  Lutz H Gade; Vincent César; Stéphane Bellemin-Laponnaz
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-13       Impact factor: 15.336

9.  Ru-catalyzed highly enantioselective hydrogenation of beta-alkyl-substituted beta-(acylamino)acrylates.

Authors:  Jing Wu; Xuanhua Chen; Rongwei Guo; Chi-hung Yeung; Albert S C Chan
Journal:  J Org Chem       Date:  2003-03-21       Impact factor: 4.354

10.  Enantioresolution of fluorinated diphenylmethanols and determination of their absolute configurations by X-Ray crystallographic and 1H NMR anisotropy methods.

Authors:  Junpei Naito; Masashi Kosaka; Takeo Sugito; Masataka Watanabe; Nobuyuki Harada; William H Pirkle
Journal:  Chirality       Date:  2004-01       Impact factor: 2.437

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  3 in total

1.  A supramolecularly tunable chiral diphosphine ligand: application to Rh and Ir-catalyzed enantioselective hydrogenation.

Authors:  Xi-Chang Zhang; Yi-Hu Hu; Chuan-Fu Chen; Qiang Fang; Li-Yao Yang; Ying-Bo Lu; Lin-Jie Xie; Jing Wu; Shijun Li; Wenjun Fang
Journal:  Chem Sci       Date:  2016-03-31       Impact factor: 9.825

2.  Synthesis of N-aryl β-amino acid derivatives via Cu(ii)-catalyzed asymmetric 1,4-reduction in air.

Authors:  Min Li; Hong-Feng Xia; Li-Yao Yang; Tao Hong; Lin-Jie Xie; Shijun Li; Jing Wu
Journal:  RSC Adv       Date:  2019-03-20       Impact factor: 4.036

3.  Mechanistic Studies Lead to Dramatically Improved Reaction Conditions for the Cu-Catalyzed Asymmetric Hydroamination of Olefins.

Authors:  Jeffrey S Bandar; Michael T Pirnot; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-11-13       Impact factor: 15.419

  3 in total

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