Asymmetric Synthesis of Di- and Trisubstituted Cyclopropanes through an Intramolecular Ring Closure

Synlett ◽  
2011 ◽  
Vol 2011 (04) ◽  
pp. 535-538 ◽  
Author(s):  
Jeffrey Kallemeyn ◽  
Mathew Mulhern ◽  
Yi-Yin Ku
Keyword(s):  
Asymmetric Synthesis ◽  
Ring Closure ◽  
Intramolecular Ring

ChemInform Abstract: Asymmetric Synthesis of Di- and Trisubstituted Cyclopropanes Through an Intramolecular Ring Closure.

ChemInform ◽  
2011 ◽  
Vol 42 (26) ◽  
pp. no-no
Author(s):  
Jeffrey M. Kallemeyn ◽  
Mathew M. Mulhern ◽  
Yi-Yin Ku
Keyword(s):  
Asymmetric Synthesis ◽  
Ring Closure ◽  
Intramolecular Ring

scholarly journals TfOH-Promoted Reaction of 2,4-Diaryl-1,1,1-Trifluorobut-3-yn-2-oles with Arenes: Synthesis of 1,3-Diaryl-1-CF3-Indenes and Versatility of the Reaction Mechanisms

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3079 ◽  
Author(s):  
Aleksey V. Zerov ◽  
Anna N. Kazakova ◽  
Irina A. Boyarskaya ◽  
Taras L. Panikorovskii ◽  
Vitalii V. Suslonov ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Reaction Mechanisms ◽  
Room Temperature ◽  
Ring Closure ◽  
Nucleophilic Attack ◽  
New Process ◽  
Intramolecular Ring ◽  
Propargyl Alcohols

The TfOH-mediated reactions of 2,4-diaryl-1,1,1-trifluorobut-3-yn-2-oles (CF3-substituted diaryl propargyl alcohols) with arenes in CH2Cl2 afford 1,3-diaryl-1-CF3-indenes in yields up to 84%. This new process for synthesis of such CF3-indenes is complete at room temperature within one hour. The synthetic potential, scope, and limitations of this reaction were illustrated by more than 70 examples. The proposed reaction mechanism invokes the formation of highly reactive CF3-propargyl cation intermediates that can be trapped at the two mesomeric positions by the intermolecular nucleophilic attack of an arene partner with a subsequent intramolecular ring closure.

INTRAMOLECULAR RING CLOSURE OF 1,2,3,4-TETRACHLORO-6-(AZULEN-1-YL)FULVENE. FORMATION OF A CYCLOHEPT[cd]-s-INDACENE DERIVATIVE

1974 ◽  
Vol 3 (3) ◽  
pp. 307-310 ◽  
Author(s):  
Ichiro Murata ◽  
Kagetoshi Yamamoto ◽  
Mitsuhisa Tamura
Keyword(s):  
Ring Closure ◽  
Intramolecular Ring
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