Enantioselective cyclopropanation reaction using a conformationally fixed pyridinium ylide through a cation-π interaction

Tetrahedron Letters

Volumn 48, Issue 5, 2007, Pages 855-858

  Yamada, Shinji ^a   Yamamoto, Jun ^a   Ohta, Emiko ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

Cation interaction; Cyclopropanation; Enantioselective reaction; Pyridinium ylide; Pyridinium interaction

Indexed keywords

ALKENE; BICYCLO COMPOUND; CATION; CYCLOPROPANE DERIVATIVE; PHENYL GROUP; PYRIDINIUM DERIVATIVE; PYRIDINIUM YLIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; CONFORMATION; CYCLOPROPANATION; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; TRANS ISOMER; X RAY ANALYSIS;

EID: 33845897635     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.142     Document Type: Article

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26. Racemic 6 was used for X-ray crystallographic analysis.
27. 2 are 0.0835 [I > 2σ(I)] and 0.2661 (all data), respectively. See CCDC 619224.
28. 2 are 0.0866 [I > 2σ(I)] and 0.2013 (all data), respectively. See CCDC 619223.
29. Instead of ylide of 2a, corresponding methyl ester was used for the DFT calculations as a model ylide to reduce conformational freedom.
30. The optimized energies for conformers I-III are -744019.268, -744017.366, and -744016.064 kcal/mol, respectively.