Literature DB >> 21366339

Origins of selectivity in Brønsted acid-promoted diazoalkane-azomethine reactions (the aza-Darzens aziridine synthesis).

Timothy L Troyer1, Hubert Muchalski, Ki Bum Hong, Jeffrey N Johnston.   

Abstract

The mechanism of the Brønsted acid-catalyzed aza-Darzens reaction is explored by charting the stereochemical outcome of the triflic acid-promoted conversion of trans-triazolines to cis-aziridines. These experiments are consistent with the intermediacy of an α-diazonium-β-amino ester intermediate.

Entities:  

Year:  2011        PMID： 21366339     DOI： 10.1021/ol200313m

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


  5 in total

1.  Evidence for a Sigmatropic and an Ionic Pathway in the Winstein Rearrangement.

Authors:  Amy A Ott; Mary H Packard; Manuel A Ortuño; Alayna Johnson; Victoria P Suding; Christopher J Cramer; Joseph J Topczewski
Journal:  J Org Chem       Date:  2018-06-14       Impact factor: 4.354

2.  Isotope effects and mechanism of the asymmetric BOROX Brønsted acid catalyzed aziridination reaction.

Authors:  Mathew J Vetticatt; Aman A Desai; William D Wulff
Journal:  J Org Chem       Date:  2013-05-21       Impact factor: 4.354

3.  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

4.  Enantiopure Calcium Iminophosphonamide Complexes: Synthesis, Photoluminescence, and Catalysis.

Authors:  Bhupendra Goswami; Thomas J Feuerstein; Ravi Yadav; Ralf Köppe; Sergei Lebedkin; Manfred M Kappes; Peter W Roesky
Journal:  Chemistry       Date:  2021-02-02       Impact factor: 5.236

5.  Synthesis of α,β-unsaturated esters of perfluoropolyalkylethers (PFPAEs) based on hexafluoropropylene oxide units for photopolymerization.

Authors:  Céline Bonneaud; Mélanie Decostanzi; Julia Burgess; Giuseppe Trusiano; Trevor Burgess; Roberta Bongiovanni; Christine Joly-Duhamel; Chadron M Friesen
Journal:  RSC Adv       Date:  2018-09-21       Impact factor: 4.036
  5 in total

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