Literature DB >> 15200313

Asymmetric aminolysis of aromatic epoxides: a facile catalytic enantioselective synthesis of anti-beta-amino alcohols.

Giuseppe Bartoli1, Marcella Bosco, Armando Carlone, Manuela Locatelli, Massimo Massaccesi, Paolo Melchiorre, Letizia Sambri.   

Abstract

[reaction: see text] The first asymmetric aminolysis of trans-aromatic epoxides with anilines is described. The process affords enantioenriched anti-beta-amino alcohols in up to 99% ee. The complete regio- and diastereoselectivity observed uses commercially available [Cr(Salen)Cl] as a Lewis acid catalyst and in combination with a very simple experimental procedure renders the present reaction a facile and practical tool for the synthesis of chiral nonracemic anti-beta-amino alcohols.

Entities:  

Year:  2004        PMID： 15200313     DOI： 10.1021/ol049372t

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


  10 in total

1.  Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes.

Authors:  Suzanne A Blum; Vicki A Rivera; Rebecca T Ruck; Forrest E Michael; Robert G Bergman
Journal:  Organometallics       Date:  2005-03-28       Impact factor: 3.876

2.  Mechanistic basis for high reactivity of (salen)Co-OTs in the hydrolytic kinetic resolution of terminal epoxides.

Authors:  Lars P C Nielsen; Stephan J Zuend; David D Ford; Eric N Jacobsen
Journal:  J Org Chem       Date:  2012-02-08       Impact factor: 4.354

3.  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

4.  Tungsten-catalyzed regio- and enantioselective aminolysis of trans-2,3-epoxy alcohols: an entry to virtually enantiopure amino alcohols.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-19       Impact factor: 15.336

5.  Gadolinium-Catalyzed Regio- and Enantioselective Aminolysis of Aromatic trans-2,3-Epoxy Sulfonamides.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-08       Impact factor: 15.336

6.  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

7.  Enantioselective cross-coupling of meso-epoxides with aryl halides.

Authors:  Yang Zhao; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2015-03-02       Impact factor: 15.419

8.  Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols.

Authors:  Gajendrasingh Ingle; Michael G Mormino; Jon C Antilla
Journal:  Org Lett       Date:  2014-10-15       Impact factor: 6.005

9.  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

10.  Tungsten-catalyzed regioselective and stereospecific ring opening of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2014-05-02       Impact factor: 15.419
  10 in total

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