Highly enantioselective cyclopropanation of styrene derivatives using Co(III)-salen complex as a catalyst

Tetrahedron

Volumn 53, Issue 21, 1997, Pages 7201-7208

  Fukuda, Tsutomu ^a,b   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030915731     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00423-7     Document Type: Article

References (47)

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40. In the reviewing process, a referee suggested use of a Co(III)-salen complex bearing electron-donating groups at C4(4′) and C5(5′) carbons. According to the suggestion, we examined the reaction of styrene and tert-butyl diazoacetate in the presence of complex i at room temperature and found that the reaction gave a 96:4 mixture of tert-butyl trans- and cis-2-phenylcyclopropane-1-carboxylate in 84%. The enantiomeric excess of the trans-isomer was 89%, which was inferior to that observed with complex (6-Br). (Chemical Equation Presented)
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44. The aldehyde was purchased from nacalai tesque and used after distillation.
45. 2O by heating at 70°C under vacuum for 2 h.
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47. 1H NMR spectroscopic data with those of tert-butyl trans- and cis-2-phenylcyclopropane-1-carboxylates (reference 3b).