Bulletin of the Chemical Society of Japan p. 445 - 451 (1994)
Update date:2022-08-04
Topics:
Miyoshi, Norikazu
Takeuchi, Seiji
Ohgo, Yoshiaki
Ketenes react with various allylic halides mediated by 2 equiv. samarium(II) diiodide (SmI2) to the ketenes to afford allylated ketones in good yields.In the reaction with γ-substituted allylic halides, the regioselectivity is influenced by the olefinic geometry of allylic halides.By using γ-substituted (E)-allylic halides, the allylation proceeds on the less hindered site (α-position) of allylic groups predominantly and the tendency was enhanced by the addition of HMPA.
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