Tetrahedron

Pentamethylcyclopentadienide in organic synthesis: nucleophilic addition of lithium pentamethylcyclopentadienide to carbonyl compounds and carbon–carbon bond …

M Uemura, K Yagi, M Iwasaki, K Nomura, H Yorimitsu…

Index: Uemura, Minoru; Yagi, Kazunari; Iwasaki, Masayuki; Nomura, Kenichi; Yorimitsu, Hideki; Oshima, Koichiro Tetrahedron, 2006 , vol. 62, # 15 p. 3523 - 3535

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Citation Number: 8

Abstract

Lithium pentamethylcyclopentadienide (C5Me5Li, Cp* Li) reacted with aromatic aldehyde to provide the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to acid or due to heating. Chlorodimethylaluminum is essential as an additive to attain the nucleophilic addition of Cp* Li to aliphatic aldehyde. The carbinol derived from aliphatic aldehyde returns to the parent ...

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