Literature DB >> 17919002

The cycloaddition of nitrones with homochiral cyclopropanes.

Katarina Sapeta1, Michael A Kerr.   

Abstract

The cycloaddition of nitrones and enantiomerically pure cyclopropane-1,1-dicarboxylates is examined. Transfer of optical activity to the adduct is dictated by thermal reaction conditions and nature of cyclopropane substitution. Optically active 2-substituted cyclopropane-1,1-dicarboxylates are shown to racemize under typical reaction conditions, providing evidence for a zwitterionic ring-opened intermediate.

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Year:  2007        PMID: 17919002     DOI: 10.1021/jo701606u

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  Cyclopentadienones via a tandem C-cyclopropylnitrone cyclization-cycloreversion sequence.

Authors:  Ihsan Erden; Christian Gärtner; Jingxiang Ma; Gabriel Cabrera; Kate Markham; Saeed Azimi; Scott Gronert
Journal:  European J Org Chem       Date:  2017-09-14

2.  Stereoselective Lewis acid mediated (3+2) cycloadditions of N-H- and N-sulfonylaziridines with heterocumulenes.

Authors:  Robert A Craig; Nicholas R O'Connor; Alexander F G Goldberg; Brian M Stoltz
Journal:  Chemistry       Date:  2014-03-06       Impact factor: 5.236

3.  Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds.

Authors:  Kyle M Lambert; Joshua B Cox; Lin Liu; Amy C Jackson; Sam Yruegas; Kenneth B Wiberg; John L Wood
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-08       Impact factor: 15.336

4.  Acetoxy-Substituted Cyclopropane Dicarbonyls as Stable Donor-Acceptor-Acceptor Cyclopropanes.

Authors:  Yahaira Reyes; Keith T Mead
Journal:  Synthesis (Stuttg)       Date:  2015-10       Impact factor: 3.157

5.  Lewis acid mediated (3 + 2) cycloadditions of donor-acceptor cyclopropanes with heterocumulenes.

Authors:  Alexander F G Goldberg; Nicholas R O'Connor; Robert A Craig; Brian M Stoltz
Journal:  Org Lett       Date:  2012-10-09       Impact factor: 6.005

6.  Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes.

Authors:  Johannes Preindl; Shyamal Chakrabarty; Jérôme Waser
Journal:  Chem Sci       Date:  2017-08-25       Impact factor: 9.825

  6 in total

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