Literature DB >> 20512797

Asymmetric catalytic aziridination of cyclic enones.

Francesco De Vincentiis1, Giorgio Bencivenni, Fabio Pesciaioli, Andrea Mazzanti, Giuseppe Bartoli, Patrizia Galzerano, Paolo Melchiorre.   

Abstract

The first catalytic method for the asymmetric aziridination of cyclic enones is described. The presented organocatalytic strategy is based on the use of an easily available organocatalyst that is able to convert a wide range of cyclic enones into the desired aziridines with very high enantiomeric purity and good chemical yield. Such a method may very well open up new opportunities to stereoselectively prepare complex chiral molecules that possess an indane moiety, a framework that is found in a large number of bioactive and pharmaceutically important molecules.

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Year:  2010        PMID: 20512797     DOI: 10.1002/asia.201000040

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  6 in total

1.  Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight.

Authors:  Shea L Johnson; Michael K Hilinski
Journal:  J Org Chem       Date:  2019-06-19       Impact factor: 4.354

2.  Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-23       Impact factor: 15.336

3.  Synthesis of 9-amino(9-deoxy)epi cinchona alkaloids, general chiral organocatalysts for the stereoselective functionalization of carbonyl compounds.

Authors:  Carlo Cassani; Rafael Martín-Rapún; Elena Arceo; Fernando Bravo; Paolo Melchiorre
Journal:  Nat Protoc       Date:  2013-01-17       Impact factor: 13.491

4.  Sterically Demanding Flexible Phosphoric Acids for Constructing Efficient and Multi-Purpose Asymmetric Organocatalysts.

Authors:  Fabian Scharinger; Ádám Márk Pálvölgyi; Melanie Weisz; Matthias Weil; Christian Stanetty; Michael Schnürch; Katharina Bica-Schröder
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-26       Impact factor: 16.823

5.  Design and synthesis of constrained bicyclic molecules as candidate inhibitors of influenza A neuraminidase.

Authors:  Cinzia Colombo; Črtomir Podlipnik; Leonardo Lo Presti; Masahiro Niikura; Andrew J Bennet; Anna Bernardi
Journal:  PLoS One       Date:  2018-02-28       Impact factor: 3.240

Review 6.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823

  6 in total

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