Nickel-catalyzed ring-opening three-component coupling of methylenecyclopropane with aldehydes and silanes

Organic Letters

Volumn 12, Issue 20, 2010, Pages 4536-4539

  Ogata, Kenichi ^a   Atsuumi, Yuka ^a   Fukuzawa, Shin Ichi ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957826990     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101838q     Document Type: Article

References (35)

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26. nBuLi.
27. In these reactions, almost all methylenecyclopropane molecules were consumed.
28. In this reaction, complex mixtures were formed.
29. CD = 21.6 Hz) assignable to the silylated alcohol attached carbon was also detected at 77.5 ppm.
30. 13C NMR.
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35. We could not rule out the possibility of mechanism via intermediate C. In nickel-catalyzed dimerization of methylenecyclopropane, the formation of a nickelacycle intermediate containing a cyclopropane ring, followed by cyclopropropenyl - butenyl rearrangement was also proposed. See: Binger, P.; Doyle, M. J.; Benn, R. Chem. Ber 1983, 116, 1, and ref 11.