Literature DB >> 29711061

Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts: A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method.

Elias J Corey1, Christopher J Helal1.   

Abstract

High enantioselectivity can be achieved when chiral oxazaborolidines are used as catalysts in the reduction of ketones by borane. In the transition state on the way to the complex chiral compounds, the two reactants are activated and held in close proximity by the catalyst, as shown below. © 1998 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Asymmetric catalysis; Boron; Ketones; Reductions; Total synthesis

Year:  1998        PMID: 29711061     DOI: 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  43 in total

1.  Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts.

Authors:  De Run Li; Anyu He; J R Falck
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

2.  Catalytic asymmetric synthesis of chiral allylic esters.

Authors:  Stefan F Kirsch; Larry E Overman
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

3.  Toward the synthesis of cobyric acid. Enantioselective syntheses of completely differentiated ring D synthons.

Authors:  Hui Wang; Carlos Tassa; Peter A Jacobi
Journal:  Org Lett       Date:  2008-06-07       Impact factor: 6.005

4.  Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: Applications for the synthesis of leucascandrolide A macrolactone.

Authors:  David R Williams; Scott V Plummer; Samarjit Patnaik
Journal:  Tetrahedron       Date:  2011-07-08       Impact factor: 2.457

5.  Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors:  Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-09-25       Impact factor: 15.419

Review 6.  Synthetic studies of viridiofungins, broad-spectrum antifungal agents and serine palmitoyl transferase inhibitors.

Authors:  Naoya Kumagai; Masakatsu Shibasaki
Journal:  J Antibiot (Tokyo)       Date:  2017-09-27       Impact factor: 2.649

Review 7.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

8.  Trapping of a cross-link formed by a major purine adduct of a metabolite of the carcinogen N-nitrosomorpholine by inorganic and biological reductants.

Authors:  Niangoran Koissi; James C Fishbein
Journal:  Chem Res Toxicol       Date:  2013-05-02       Impact factor: 3.739

9.  Enantioselective total synthesis of (-)-acutumine.

Authors:  Fang Li; Samuel S Tartakoff; Steven L Castle
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

10.  Stereochemical and skeletal diversity arising from amino propargylic alcohols.

Authors:  Daniela Pizzirani; Taner Kaya; Paul A Clemons; Stuart L Schreiber
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

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