Tetrahedron p. 9467 - 9474 (2006)
Update date:2022-08-05
Topics:
Takanami, Toshikatsu
Hayashi, Mikiko
Iso, Kazuhiro
Nakamoto, Hirose
Suda, Kohji
The Claisen rearrangement of simple aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin, Cr(TPP)Cl, is described. The porphyrin-based Lewis acid catalyst can effectively accelerate the rearrangement via a concerted [3,3] pathway with a minimal degree of bond ionization of the substrates, providing the corresponding Claisen products in moderate to high yields and almost perfect regioselectivity at low catalyst loading.
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Doi:10.1021/jo00180a025
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