Tetrahedron

Intramolecular carbolithiation promoted by a DTBB-catalysed chlorine–lithium exchange

M Yus, R Ortiz, FF Huerta

文献索引：Yus, Miguel; Ortiz, Rosa; Huerta, Fernando F. Tetrahedron, 2003 , vol. 59, # 43 p. 8525 - 8542

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被引用次数: 28

摘要

The reaction of 6-chlorohex-1-ene 1 with lithium powder and a catalytic amount of 4, 4′-di- tert-butylbiphenyl (DTBB, 5% molar) in THF at− 78° C gives the corresponding organolithium intermediate 2, which by reaction with different electrophiles affords, after hydrolysis with diluted hydrochloric acid, the expected products 3. The same reaction performed at− 30° C gives cyclopentyl derivatives 5, probably by cyclisation of the open-chain intermediate 2 to ...