Stereoselective 1,4-silaboration of 1,3-dienes catalyzed by nickel complexes

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1567-1569

  Suginome, Michinori ^a   Matsuda, Takanori ^a   Yoshimoto, Takayo ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001205903     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990908y     Document Type: Article

References (40)

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31. 2 (25.7 mg. 0.10 mmol) and 1,3-diene (2 equiv based on 1) in a Schlenk tube was added DIBAH (0.2 M solution in toluene, 1.0 mL) at 0°C. The mixture was stirred for 30 min at 0°C. To the mixture was added 1 (521 mg, 2.0 mmol); the mixture was heated at 80°C for 24 h. Evaporation of volatile materials followed by bulb-to-bulb distillation afforded the products.
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35. Palladium-phosphine and palladium-phosphite complexes were also ineffective for the reaction.
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37. The regio- and stereochemical assignments were made by NOE experiments of the silaboration products or by transformation to homoallylic alcohols through reactions with benzaldehyde.
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40. The reaction afforded 7a in 80% yield in the presence of 2 mol % of the Ni catalyst.