Literature DB >> 16209487

Catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water.

Stéphane Azoulay1, Kei Manabe, Shü Kobayashi.   

Abstract

[reaction: see text] An operationally simple and environmentally benign protocol for the catalytic asymmetric ring opening of meso-epoxides with aromatic amines has been developed. The reactions proceeded smoothly in the presence of 1 mol % of Sc(OSO3C12H25)3 and 1.2 mol % of a chiral bipyridine ligand in water to afford beta-amino alcohols in high yields with excellent enantioselectivities.

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Year:  2005        PMID： 16209487     DOI： 10.1021/ol051546z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.

Authors:  David E White; Pamela M Tadross; Zhe Lu; Eric N Jacobsen
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

Review 2.  Organic synthesis "on water".

Authors:  Arani Chanda; Valery V Fokin
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622

Review 3.  Synthesis and Application of the Transition Metal Complexes of α-Pyridinyl Alcohols, α-Bipyridinyl Alcohols, α,α'-Pyridinyl Diols and α,α'-Bipyridinyl Diols in Homogeneous Catalysis.

Authors:  Tegene Tole; Johannes Jordaan; Hermanus Vosloo
Journal:  Molecules       Date:  2018-04-12       Impact factor: 4.411

4.  γ-, Diastereo-, and Enantioselective Addition of MEMO-Substituted Allylboron Compounds to Aldimines Catalyzed by Organoboron-Ammonium Complexes.

Authors:  Ryan J Morrison; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-01       Impact factor: 15.336

5.  Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal-organic frameworks as recyclable heterogeneous catalysts.

Authors:  Koichi Tanaka; Maya Kinoshita; Jun Kayahara; Yutaro Uebayashi; Kazusada Nakaji; Maja Morawiak; Zofia Urbanczyk-Lipkowska
Journal:  RSC Adv       Date:  2018-08-06       Impact factor: 3.361

6.  Highly Diastereoselective Construction of Carbon- Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates.

Authors:  Magdalena Rapp; Klaudia Margas-Musielak; Patrycja Kaczmarek; Agnieszka Witkowska; Tomasz Cytlak; Tomasz Siodła; Henryk Koroniak
Journal:  Front Chem       Date:  2021-06-02       Impact factor: 5.221

Review 7.  Organocatalyzed enantioselective desymmetrization of aziridines and epoxides.

Authors:  Ping-An Wang
Journal:  Beilstein J Org Chem       Date:  2013-08-15       Impact factor: 2.883
  7 in total

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