Literature DB >> 21265519

Dynamic chirality of (E)-5-cyclononen-1-one and its enolate.

Katsuhiko Tomooka1, Takayuki Ezawa, Hiroko Inoue, Kazuhiro Uehara, Kazunobu Igawa.   

Abstract

It has been found that (E)-5-cyclononen-1-one (2a) exhibits marginal planar chirality owing to an insufficient topological constraint, whereas the enolates 3 derived from 2a show robust planar chirality. Enantioenriched enolates are easily prepared by enzymatic hydrolysis, and they show an ability to serve as chiral nucleophiles.

Entities:  

Year:  2011        PMID： 21265519     DOI： 10.1021/ja1092375

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  4 in total

1.  AlCl₃-Catalyzed Ring Expansion Cascades of Bicyclic Cyclobutenamides Involving Highly Strained Cis,Trans-Cycloheptadienone Intermediates.

Authors:  Xiao-Na Wang; Elizabeth H Krenske; Ryne C Johnston; K N Houk; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2015-04-20       Impact factor: 15.419

2.  Enantioselective catalytic transannular ketone-ene reactions.

Authors:  Naomi S Rajapaksa; Eric N Jacobsen
Journal:  Org Lett       Date:  2013-08-08       Impact factor: 6.005

3.  9-Membered Carbocycles: Strategies and Tactics for their Synthesis.

Authors:  Tatjana Huber; Raphael E Wildermuth; Thomas Magauer
Journal:  Chemistry       Date:  2018-03-13       Impact factor: 5.236

4.  Torquoselective ring opening of fused cyclobutenamides: evidence for a cis,trans-cyclooctadienone intermediate.

Authors:  Xiao-Na Wang; Elizabeth H Krenske; Ryne C Johnston; K N Houk; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2014-07-03       Impact factor: 15.419
  4 in total

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