Olefin cyclopropanation with aryl diazocompounds upon catalysis by a dirhodium(II) complex

Tetrahedron Letters

Volumn 52, Issue 10, 2011, Pages 1136-1139

  Verdecchia, Mirella ^a   Tubaro, Cristina ^a   Biffis, Andrea ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

Asymmetric catalysis; Cyclopropanation; Phenyldiazomethane; Rhodium

Indexed keywords

ALKENE; AZO COMPOUND; CYCLOPROPANE; DIAZO COMPOUND; DIRHODIUM COMPLEX; ENOL ETHER; METAL COMPLEX; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CYCLOPROPANATION; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 79551687563     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.002     Document Type: Article

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24. General procedure for the catalytic tests. Complex I (15 μmol or 30 μmol) and olefin (15 mmol or 30 mmol) were dissolved in 20 mL 1:1 toluene/tetrahydrofuran under an inert argon atmosphere. To this solution, the diazocompound solution (1.5 mmol), freshly prepared as described in Ref. 12, was added over a 5 h period using a syringe pump. The reaction mixture was left under stirring overnight at room temperature, after which it was evaporated to dryness under reduced pressure. The resulting oil was then purified by column chromatography over silica gel (petroleum ether/ethyl acetate, 98:2 v:v) to afford the cyclopropanation products. The configuration of the various diastereoisomers was attributed by comparing their NMR spectra with those of the pure diastereoisomers previously reported in the literature.
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