Literature DB >> 22707800

Anomalies in the asymmetric transfer hydrogenation of several polycyclic meso compounds.

David R Clay1, Matthias C McIntosh.   

Abstract

Over the course of developing a multigram scale preparation of epoxy quinol 1 via asymmetric transfer hydrogenation (ATH) using the Noyori Ru(arene)(S,S-TsDPEN) catalysts, we observed several unexpected phenomena, including (i) chemoselective alkene vs ketone reduction of an enedione, (ii) a significant arene ligand effect (p-cymene vs. mesitylene) on the reaction pathway, and (iii) solvent-based reversal of the sense of enantioinduction.

Entities:  

Year:  2012        PMID： 22707800      PMCID： PMC3374411          DOI： 10.1016/j.tetlet.2011.12.123

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  19 in total

1.  No-D NMR (no-deuterium proton NMR) spectroscopy: a simple yet powerful method for analyzing reaction and reagent solutions.

Authors:  Thomas R Hoye; Brian M Eklov; Troy D Ryba; Mikhail Voloshin; Letitia J Yao
Journal:  Org Lett       Date:  2004-03-18       Impact factor: 6.005

2.  Realistic modeling of ruthenium-catalyzed transfer hydrogenation.

Authors:  Jan-Willem Handgraaf; Evert Jan Meijer
Journal:  J Am Chem Soc       Date:  2007-02-24       Impact factor: 15.419

Review 3.  Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts.

Authors:  Takao Ikariya; A John Blacker
Journal:  Acc Chem Res       Date:  2007-10-26       Impact factor: 22.384

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.  Antascomicins A, B, C, D and E. Novel FKBP12 binding compounds from a Micromonospora strain.

Authors:  T Fehr; J J Sanglier; W Schuler; L Gschwind; M Ponelle; W Schilling; C Wioland
Journal:  J Antibiot (Tokyo)       Date:  1996-03       Impact factor: 2.649

6.  Efficient, scalable asymmetric synthesis of an epoxy quinol via Noyori desymmetrization of a meso diketone.

Authors:  David R Clay; Ashley G Rosenberg; Matthias C McIntosh
Journal:  Tetrahedron Asymmetry       Date:  2011-04-10

7.  Synthesis of the C21-C34 fragment of antascomicin B.

Authors:  John M Hutchison; Andrew S Gibson; David T Williams; Matthias C McIntosh
Journal:  Tetrahedron Lett       Date:  2011-10-30       Impact factor: 2.415

8.  Origin of enantioselectivity in the Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones.

Authors:  Peter Brandt; Peter Roth; Pher G Andersson
Journal:  J Org Chem       Date:  2004-07-23       Impact factor: 4.354

9.  Ru-TsDPEN with formic acid/Hunig's base for asymmetric transfer hydrogenation, a practical synthesis of optically enriched N-propyl pantolactam.

Authors:  Ji Zhang; Peter G Blazecka; Michelle M Bruendl; Yun Huang
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

10.  Toward the Synthesis of Antascomicin B. Synthesis of a Model of the C22-C34 Fragment via Ireland-Claisen and Allylic Diazene Rearrangements.

Authors:  Wei Qi; Matthias C McIntosh
Journal:  Tetrahedron       Date:  2008       Impact factor: 2.457
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