Literature DB >> 23265391

Chemoselective allene aziridination via Ag(I) catalysis.

Jared W Rigoli1, Cale D Weatherly, Brian T Vo, Samuel Neale, Alan R Meis, Jennifer M Schomaker.   

Abstract

Allene aziridination generates useful bicyclic methylene aziridine scaffolds that can be flexibly transformed into a range of stereochemically complex and densely functionalized amine-containing stereotriads. The scope of this chemistry has been limited by the poor chemoselectivity that often results when typical dinuclear Rh(II) catalysts are employed with homoallenic carbamates. Herein, Ag(I) catalysts that significantly improve the scope and yield of bicyclic methylene aziridines that can be prepared via allene aziridination are described.

Entities:  

Year:  2012        PMID： 23265391      PMCID： PMC4490828          DOI： 10.1021/ol303167n

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


  29 in total

1.  A silver-catalyzed intramolecular amidation of saturated C--h bonds.

Authors:  Yong Cui; Chuan He
Journal:  Angew Chem Int Ed Engl       Date:  2004-08-13       Impact factor: 15.336

2.  Catalytic intermolecular amination of C-H bonds: method development and mechanistic insights.

Authors:  Kristin Williams Fiori; J Du Bois
Journal:  J Am Chem Soc       Date:  2007-01-24       Impact factor: 15.419

3.  Rh(II)-catalysed room temperature aziridination of homoallyl-carbamates.

Authors:  Christopher J Hayes; Peter W Beavis; Lesley A Humphries
Journal:  Chem Commun (Camb)       Date:  2006-11-21       Impact factor: 6.222

4.  A diruthenium catalyst for selective, intramolecular allylic C-H amination: reaction development and mechanistic insight gained through experiment and theory.

Authors:  Mark Edwin Harvey; Djamaladdin G Musaev; J Du Bois
Journal:  J Am Chem Soc       Date:  2011-10-07       Impact factor: 15.419

5.  Cobalt-catalyzed efficient aziridination of alkenes.

Authors:  Guang-Yao Gao; Jeremiah D Harden; X Peter Zhang
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

6.  Modular functionalization of allenes to aminated stereotriads.

Authors:  Christopher S Adams; Luke A Boralsky; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2012-06-20       Impact factor: 15.419

7.  Expanding the scope of C-H amination through catalyst design.

Authors:  Christine G Espino; Kristin Williams Fiori; Mihyong Kim; J Du Bois
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

8.  Mechanism of the iron-mediated alkene aziridination reaction: experimental and computational investigations.

Authors:  Katie L Klotz; Luke M Slominski; Miranda E Riemer; James A Phillips; Jason A Halfen
Journal:  Inorg Chem       Date:  2009-02-02       Impact factor: 5.165

9.  Silver(I) coordination chemistry of 2,6-diarylpyrazines. Pi-stacking, anion coordination, and steric control.

Authors:  Nate Schultheiss; Douglas R Powell; Eric Bosch
Journal:  Inorg Chem       Date:  2003-08-25       Impact factor: 5.165

10.  Introducing a mixed-valent dirhodium(II,III) catalyst with increased stability in C-H amination.

Authors:  Katherine P Kornecki; John F Berry
Journal:  Chem Commun (Camb)       Date:  2012-11-07       Impact factor: 6.222
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  9 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.  Arene C-H amination at nickel in terphenyl-diphosphine complexes with labile metal-arene interactions.

Authors:  David E Herbert; Nadia C Lara; Theodor Agapie
Journal:  Chemistry       Date:  2013-10-14       Impact factor: 5.236

3.  A Stereoselective [3+1] Ring Expansion for the Synthesis of Highly Substituted Methylene Azetidines.

Authors:  Steven C Schmid; Ilia A Guzei; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-01       Impact factor: 15.336

4.  Inverting Steric Effects: Using "Attractive" Noncovalent Interactions To Direct Silver-Catalyzed Nitrene Transfer.

Authors:  Minxue Huang; Tzuhsiung Yang; Jonathan D Paretsky; John F Berry; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2017-11-20       Impact factor: 15.419

5.  Tunable Aziridinium Ylide Reactivity: Non-covalent Interactions Enable Divergent Product Outcomes.

Authors:  Kate A Nicastri; Soren Zappia; Jared C Pratt; Julia M Duncan; Ilia A Guzei; Israel Fernández; Jennifer M Schomaker
Journal:  ACS Catal       Date:  2022-01-11       Impact factor: 13.084

6.  Oxidative allene amination for the synthesis of nitrogen-containing heterocycles.

Authors:  Josephine Eshon; Nels C Gerstner; Jennifer M Schomaker
Journal:  ARKIVOC       Date:  2018-11-26       Impact factor: 1.140

7.  Tunable, chemoselective amination via silver catalysis.

Authors:  Jared W Rigoli; Cale D Weatherly; Juliet M Alderson; Brian T Vo; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2013-11-11       Impact factor: 15.419

8.  Aminodiols via stereocontrolled oxidation of methyleneaziridines.

Authors:  Jared W Rigoli; Ilia A Guzei; Jennifer M Schomaker
Journal:  Org Lett       Date:  2014-03-11       Impact factor: 6.005

Review 9.  Synthesis and applications of methyleneaziridines.

Authors:  Bin Pan; Feng Li; Yingying Zhao
Journal:  RSC Adv       Date:  2020-10-27       Impact factor: 4.036
  9 in total

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