Literature DB >> 19173352

Catalytic, enantioselective ring opening of aziridines.

Christoph Schneider1.   

Abstract

Cooperative metal centers in a bimetallic catalyst facilitate the highly enantioselective ring opening of meso aziridines 1 with silyl nucleophiles (see scheme; TMS = trimethylsilyl). The 1,2-azidoamides 2 and 1,2-amidonitriles 3 obtained in this way in high yields and with up to 99% ee are valuable precursors to enantiomerically pure 1,2-diamines and beta-amino acids.

Entities:  

Year:  2009        PMID: 19173352     DOI: 10.1002/anie.200805542

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  14 in total

1.  Chemo- and Enantioselective Intramolecular Silver-Catalyzed Aziridinations.

Authors:  Minsoo Ju; Cale D Weatherly; Ilia A Guzei; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

2.  Elucidation of the Reaction Mechanism of C2 + N1 Aziridination from Tetracarbene Iron Catalysts.

Authors:  Sara B Isbill; Preeti P Chandrachud; Jesse L Kern; David M Jenkins; Sharani Roy
Journal:  ACS Catal       Date:  2019-05-31       Impact factor: 13.084

3.  Hydrogen bonds determine the structures of the ternary heterocyclic complexes C₂H₄O···2HF, C₂H₅N···2HF and C₂H₄S···2HF: density functional theory and topological calculations.

Authors:  Boaz G Oliveira; Regiane C M U Araújo; Antônio B Carvalho; Mozart N Ramos
Journal:  J Mol Model       Date:  2011-02-08       Impact factor: 1.810

4.  N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines.

Authors:  Hao Tan; Samya Samanta; Asim Maity; Pritam Roychowdhury; David C Powers
Journal:  Nat Commun       Date:  2022-06-10       Impact factor: 17.694

5.  Rhodium(III)-Catalyzed Three-Component 1,2-Diamination of Unactivated Terminal Alkenes.

Authors:  Sumin Lee; Young Jin Jang; Erik J T Phipps; Honghui Lei; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2020       Impact factor: 3.157

6.  Chiral phosphoric acid-catalyzed desymmetrization of meso-aziridines with functionalized mercaptans.

Authors:  Shawn E Larson; Juan C Baso; Guilong Li; Jon C Antilla
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

7.  Kinetics and mechanism of vanadium catalysed asymmetric cyanohydrin synthesis in propylene carbonate.

Authors:  Michael North; Marta Omedes-Pujol
Journal:  Beilstein J Org Chem       Date:  2010-11-03       Impact factor: 2.883

8.  Palladium-Catalyzed, Enantioselective Desymmetrization of N-Acylaziridines with Indoles.

Authors:  Kinney Van Hecke; Tyler R Benton; Michael Casper; Dustin Mauldin; Brandon Drake; Jeremy B Morgan
Journal:  Org Lett       Date:  2021-10-05       Impact factor: 6.072

9.  Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines.

Authors:  Hongnan Sun; Binbin Huang; Run Lin; Chao Yang; Wujiong Xia
Journal:  Beilstein J Org Chem       Date:  2015-04-22       Impact factor: 2.883

10.  Crystal structure of 1-[(2,4,6-triiso-propyl-phen-yl)sulfon-yl]aziridine.

Authors:  Lena Knauer; Christopher Golz; Carsten Strohmann
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-06-03
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