Highly regioselective [3,3] rearrangement of aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin complex, Cr(TPP)Cl

作者:Takanami Toshikatsu; Hayashi Mikiko; Iso Kazuhiro; Nakamoto Hirose; Suda Kohji*
来源:Tetrahedron, 2006, 62(40): 9467-9474.
DOI:10.1016/j.tet.2006.07.051

摘要

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.

  • 出版日期2006-10-2