Literature DB >> 11971692

Highly enantioselective hydrosilylation of aromatic alkenes.

Jakob F Jensen1, Bo Y Svendsen, Thomas V la Cour, Henriette L Pedersen, Mogens Johannsen.   

Abstract

Currently, the most effective and economic way to convert an alkene into an optically active alcohol is the two-step sequence: hydrosilylation/oxidation. Much work has been devoted to elucidating effective catalysts for this process, but hitherto only one effective and highly stereoselective process has been available. Herein we present a novel catalytic system for the asymmetric hydrosilylation of aromatic alkenes, giving the products in high yields and with the highest enantioselectivity (up to 99% ee) ever observed for this reaction. The reaction works efficiently for a variety of substituted aromatic alkenes, giving access after Tamao oxidation to almost optically pure benzylic alcohols in high yields.

Entities:  

Year:  2002        PMID: 11971692     DOI: 10.1021/ja025617q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  8 in total

1.  Catalytic enantioselective conjugate allylation of unsaturated methylidene ketones.

Authors:  Laura A Brozek; Joshua D Sieber; James P Morken
Journal:  Org Lett       Date:  2011-02-02       Impact factor: 6.005

2.  Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes.

Authors:  Christopher H Schuster; Bo Li; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

3.  Asymmetric Ni-catalyzed conjugate allylation of activated enones.

Authors:  Joshua D Sieber; James P Morken
Journal:  J Am Chem Soc       Date:  2008-03-14       Impact factor: 15.419

4.  Catalytic enantioselective allylation of dienals through the intermediacy of unsaturated pi-allyl complexes.

Authors:  Ping Zhang; James P Morken
Journal:  J Am Chem Soc       Date:  2009-09-09       Impact factor: 15.419

5.  New biphenol-based, fine-tunable monodentate phosphoramidite ligands for catalytic asymmetric transformations.

Authors:  Zihao Hua; Victor C Vassar; Hojae Choi; Iwao Ojima
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-12       Impact factor: 11.205

6.  Synthesis and characterization of privileged monodentate phosphoramidite ligands and chiral Brønsted acids derived from d-mannitol.

Authors:  Abdullah Mohammed A Al-Majid; Assem Barakat; Yahia Nasser Mabkhot; Mohammad Shahidul Islam
Journal:  Int J Mol Sci       Date:  2012-02-29       Impact factor: 6.208

7.  Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles.

Authors:  Michael W Gribble; Michael T Pirnot; Jeffrey S Bandar; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2017-02-01       Impact factor: 15.419

8.  Ligands with 1,10-phenanthroline scaffold for highly regioselective iron-catalyzed alkene hydrosilylation.

Authors:  Meng-Yang Hu; Qiao He; Song-Jie Fan; Zi-Chen Wang; Luo-Yan Liu; Yi-Jiang Mu; Qian Peng; Shou-Fei Zhu
Journal:  Nat Commun       Date:  2018-01-15       Impact factor: 14.919

  8 in total

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