Literature DB >> 16339409

Asymmetric hydrogenation of unfunctionalized, purely alkyl-substituted olefins.

Sharon Bell1, Bettina Wüstenberg, Stefan Kaiser, Frederik Menges, Thomas Netscher, Andreas Pfaltz.   

Abstract

Asymmetric hydrogenation of olefins is one of the most useful reactions for the synthesis of optically active compounds, especially in industry. However, the application range of the catalysts developed so far is limited to alkenes with a coordinating functional group or an aryl substituent next to the double bond. We have found a class of chiral iridium catalysts that give high enantioselectivity in the hydrogenation of unfunctionalized, trialkyl-substituted olefins. Because these catalysts do not require the presence of any particular functional group or aryl substituent in the substrate, they considerably broaden the scope of asymmetric hydrogenation.

Entities:  

Year:  2005        PMID: 16339409     DOI: 10.1126/science.1121977

Source DB:  PubMed          Journal:  Science        ISSN: 0036-8075            Impact factor:   47.728


  10 in total

1.  Ethylene in organic synthesis. Repetitive hydrovinylation of alkenes for highly enantioselective syntheses of pseudopterosins.

Authors:  Daniel J Mans; G Adam Cox; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

2.  Asymmetric hydrovinylation of vinylindoles. A facile route to cyclopenta[g]indole natural products (+)-cis-trikentrin A and (+)-cis-trikentrin B.

Authors:  Wang Liu; Hwan Jung Lim; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2012-03-13       Impact factor: 15.419

3.  ORGANIC CHEMISTRY. Catalytic asymmetric hydroamination of unactivated internal olefins to aliphatic amines.

Authors:  Yang Yang; Shi-Liang Shi; Dawen Niu; Peng Liu; Stephen L Buchwald
Journal:  Science       Date:  2015-07-03       Impact factor: 47.728

4.  Widely applicable synthesis of enantiomerically pure tertiary alkyl-containing 1-alkanols by zirconium-catalyzed asymmetric carboalumination of alkenes and palladium- or copper-catalyzed cross-coupling.

Authors:  Shiqing Xu; Ching-Tien Lee; Guangwei Wang; Ei-ichi Negishi
Journal:  Chem Asian J       Date:  2013-05-13

Review 5.  Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors:  Keary M Engle; Jin-Quan Yu
Journal:  J Org Chem       Date:  2013-05-03       Impact factor: 4.354

6.  Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis.

Authors:  Patrick D Parker; Xintong Hou; Vy M Dong
Journal:  J Am Chem Soc       Date:  2021-04-23       Impact factor: 16.383

7.  Application of phosphine-phosphite ligands in the iridium catalyzed enantioselective hydrogenation of 2-methylquinoline.

Authors:  Miguel Rubio; Antonio Pizzano
Journal:  Molecules       Date:  2010-10-29       Impact factor: 4.411

8.  Inverting External Asymmetric Induction via Selective Energy Transfer Catalysis: A Strategy to β-Chiral Phosphonate Antipodes.

Authors:  Carina Onneken; Kathrin Bussmann; Ryan Gilmour
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336

9.  A Modular Synthesis of Teraryl-Based α-Helix Mimetics, Part 4: Core Fragments with Two Halide Leaving Groups Featuring Side Chains of Proteinogenic Amino Acids.

Authors:  Melanie Trobe; Julia Blesl; Martin Vareka; Till Schreiner; Rolf Breinbauer
Journal:  European J Org Chem       Date:  2022-02-24

10.  Enzymatic Asymmetric Reduction of Unfunctionalized C=C Bonds with Archaeal Geranylgeranyl Reductases.

Authors:  Richard Cervinka; Daniel Becker; Steffen Lüdeke; Sonja-Verena Albers; Thomas Netscher; Michael Müller
Journal:  Chembiochem       Date:  2021-07-22       Impact factor: 3.164

  10 in total

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