Literature DB >> 21627092

Chiral Brønsted acid-catalyzed asymmetric trisubstituted aziridine synthesis using α-diazoacyl oxazolidinones.

Takuya Hashimoto1, Hiroki Nakatsu, Kumiko Yamamoto, Keiji Maruoka.   

Abstract

Despite the remarkable advances in catalytic asymmetric aziridinations over the past decades, establishing a general procedure for the stereoselective synthesis of trisubstituted aziridines has remained an elusive goal. Chiral N-triflyl phosphoramide-catalyzed reactions of N-α-diazoacyl oxazolidinones and N-Boc imines were developed as a solution to this unmet challenge.

Entities:  

Year:  2011        PMID: 21627092     DOI: 10.1021/ja203901h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  5 in total

1.  CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines.

Authors:  Haoxuan Wang; Jeffrey C Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2017-06-15       Impact factor: 15.419

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.  Three-component synthesis of highly functionalized aziridines containing a peptide side chain and their one-step transformation into β-functionalized α-ketoamides.

Authors:  Lena Huck; Juan F González; Elena de la Cuesta; J Carlos Menéndez
Journal:  Beilstein J Org Chem       Date:  2016-08-08       Impact factor: 2.883

4.  Chiral Brønsted Acid-Catalyzed Asymmetric Synthesis of N-Aryl-cis-aziridine Carboxylate Esters.

Authors:  Sean P Bew; John Liddle; David L Hughes; Paolo Pesce; Sean M Thurston
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-05       Impact factor: 15.336

5.  Asymmetric Brønsted acid-catalyzed aza-Diels-Alder reaction of cyclic C-acylimines with cyclopentadiene.

Authors:  Magnus Rueping; Sadiya Raja
Journal:  Beilstein J Org Chem       Date:  2012-10-23       Impact factor: 2.883

  5 in total

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