Highly enantioselective and cis-diastereoselective cyclopropanation of olefins catalyzed by ruthenium complexes of (iminophosphoranyl)ferrocenes

Tetrahedron Letters

Volumn 48, Issue 45, 2007, Pages 8014-8017

  Hoang, Vo D M ^a   Reddy, Pattubala A N ^a   Kim, Tae Jeong ^a  

^a Kyungpook National University   (South Korea)

Author keywords

(Iminophosphoranyl)ferrocenes; Asymmetric cyclopropanation; cis Diastereoselection; Ruthenium catalysts

Indexed keywords

DIAZOACETIC ACID ETHYL ESTER; FERROCENE DERIVATIVE; LIGAND; METAL; RUTHENIUM; RUTHENIUM COMPLEX; STYRENE;

ARTICLE; CATALYSIS; CHIRALITY; CIS ISOMER; COMPLEX FORMATION; CYCLOPROPANATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; LIGAND BINDING; METAL BINDING; REACTION ANALYSIS;

EID: 35148831172     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.035     Document Type: Article

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50. 2 in dichloroethane (10 mL). This solution was mixed with the olefin substrate (10 equiv). To the reaction mixture at 70 °C was added slowly α-ethyldiazoacetate (2.5 mmol) diluted in dichloroethane (10 mL) over a period of 15 h with a syringe pump. After the addition was complete, the solvent and excess olefin were removed under vacuum. The oily residue was passed through a short silica gel column and the products were collected. The diastereomeric excess (% de) was determined by GC equipped with CBP-10 on a Acme 6000E GC. The enationmetric excess (% ee) was determined by GC equipped with Chiraldex BPH on a Acme 6000E GC. The absolute configuration of enatiomer was determined by comparison of their specific rotation with previous reports.