ホモアリルアルコールのレトロアリル化を利用した選択的有機合成反応の開発 [in Japanese] Selective Reactions Based on Retro-allylation of Homoallyl Alcohols [in Japanese]
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Metal-mediated or -catalyzed retro-allylation of homoallyl alcohol has emerged as a new useful method for preparing allylmetals. The metal alkoxides of well-designed homoallyl alcohols undergo retro-allylation via chairlike six-membered transition states. Thanks to the rigid transition states, the retro-allylation reactions proceed regio- and stereo specifically, yielding regio- and stereochemically well-defined allylmetals. The allylmetals thus generated are used in situ, which can afford allylated products with high selectivity. Retro-allylation reactions mediated by zirconium, gallium, palladium, and rhodium are described. Reversible additions of pentamethylcyclopentadienyl anion to carbonyl compounds are also described.
- J. Synth. Org. Chem. Jpn.
J. Synth. Org. Chem. Jpn. 66(4), 332-343, 2008-04-01
The Society of Synthetic Organic Chemistry, Japan