Copper-catalyzed addition reaction of γ,γ-dialkoxyallylic zirconium species with imines

Tetrahedron Letters

Volumn 46, Issue 48, 2005, Pages 8381-8383

  Sato, Azusa ^a   Ito, Hisanaka ^b   Okada, Midori ^a   Nakamura, Yuko ^a   Taguchi, Takeo ^b  

^a TOKYO WOMEN'S MEDICAL UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

, Dialkoxyallylic zirconium species; Allylation; Copper; Imine; Transmetalation

Indexed keywords

ANION; COPPER; IMINE; ZIRCONIUM DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; STEREOCHEMISTRY; TEMPERATURE;

EID: 27644590384     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.144     Document Type: Article

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38. 2 (351 mg, 1.2 mmol) and n-BuLi (1.42 M hexane solution, 1.69 mL, 2.4 mmol) in toluene (5 mL) was stirred at -78°C for 1 h, and then to this was added triethyl orthoacrylate (174 mg, 1 mmol). After being stirred for 3 h at room temperature, the mixture was cooled at -78°C. To this was added CuCN (90 mg, 1 mmol) and a solution of benzylideneaniline (217 mg, 1.2 mmol) in THF (5 mL) and the whole was stirred for total 8 h at 0°C at the beginning, then allowing to warm very slowly to room temperature. Extractive work-up followed by silica gel column chromatography (hexane-AcOEt, 10:1) gave N-(2,2-diethoxy-1- phenyl-3-butenyl)aniline 3a (261 mg, 84% yield).