Literature DB >> 29242861

Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.

Vladimir Maslivetc1, Colby Barrett, Nicolai A Aksenov, Marina Rubina, Michael Rubin.   

Abstract

An unusual reaction is described, involving a formal intramolecular nucleophilic substitution of bromocyclopropanes with nitrogen ylides generated in situ from N-benzyl carboxamides. It is shown that this reaction involves cyclopropene intermediates and allows for the facile and expeditious preparation of 3-azabicyclo[3.1.0]hexan-2-one scaffolds.

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Year:  2018        PMID： 29242861      PMCID： PMC5755969          DOI： 10.1039/c7ob02068f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  52 in total

1.  Catalytic enantioselective hydrostannation of cyclopropenes.

Authors:  Marina Rubina; Michael Rubin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2004-03-31       Impact factor: 15.419

2.  Modulable and highly diastereoselective carbometalations of cyclopropenes.

Authors:  Dorian Didier; Pierre-Olivier Delaye; Marwan Simaan; Biana Island; Guillaume Eppe; Hendrik Eijsberg; Amir Kleiner; Paul Knochel; Ilan Marek
Journal:  Chemistry       Date:  2013-12-12       Impact factor: 5.236

3.  Cyclopropene derivatives as precursors to enantioenriched cyclopropanols and n-butenals possessing quaternary carbon stereocenters.

Authors:  Marwan Simaan; Pierre-Olivier Delaye; Min Shi; Ilan Marek
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-16       Impact factor: 15.336

4.  Cyclization of lithiated pyridine and quinoline carboxamides: synthesis of partially saturated pyrrolopyridines and spirocyclic beta-lactams.

Authors:  Jonathan Clayden; Stuart D Hamilton; Rukhsana T Mohammed
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

5.  Transition metal-catalyzed hydro-, sila-, and stannastannation of cyclopropenes: stereo- and regioselective approach toward multisubstituted cyclopropyl synthons.

Authors:  Marina Rubina; Michael Rubin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2002-10-02       Impact factor: 15.419

6.  Synthesis of Chiral Aminocyclopropanes by Rare-Earth-Metal-Catalyzed Cyclopropene Hydroamination.

Authors:  Huai-Long Teng; Yong Luo; Baoli Wang; Liang Zhang; Masayoshi Nishiura; Zhaomin Hou
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-11       Impact factor: 15.336

7.  Catalytic enantioselective hydroboration of cyclopropenes.

Authors:  Marina Rubina; Michael Rubin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2003-06-18       Impact factor: 15.419

8.  Directed carbozincation reactions of cyclopropene derivatives.

Authors:  Vinod Tarwade; Xiaozhong Liu; Ni Yan; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2009-04-22       Impact factor: 15.419

9.  Brook Rearrangement as a Trigger for the Ring Opening of Strained Carbocycles.

Authors:  Fa-Guang Zhang; Guillaume Eppe; Ilan Marek
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-14       Impact factor: 15.336

10.  Second-generation highly potent and selective inhibitors of the hepatitis C virus NS3 serine protease.

Authors:  Kevin X Chen; Latha Nair; Bancha Vibulbhan; Weiying Yang; Ashok Arasappan; Stephane L Bogen; Srikanth Venkatraman; Frank Bennett; Weidong Pan; Melissa L Blackman; Angela I Padilla; Andrew Prongay; Kuo-Chi Cheng; Xiao Tong; Neng-Yang Shih; F George Njoroge
Journal:  J Med Chem       Date:  2009-03-12       Impact factor: 7.446
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  1 in total

1.  Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates.

Authors:  Vladimir A Maslivetc; Liliya V Frolova; Snezna Rogelj; Anna A Maslivetc; Marina Rubina; Michael Rubin
Journal:  J Org Chem       Date:  2018-10-30       Impact factor: 4.354
  1 in total

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