T. Imai, S. Nishida
Aug 1, 1990
Citations
0
Influential Citations
37
Citations
Journal
Journal of Organic Chemistry
Abstract
Epichlorohydrin (1) was allylated in good yields with representative allylic silanes and stannanes in the presence of appropriate Lewis acids. The reaction proceeds with ring opening at the unsubstituted site in 1 and with allylic inversion in the allylating agents to give 1-chloro-5-alken-2-ols cleanly. A short synthesis of (S)-(-)-ipsenol from 1 and an (allenylmethyl) silane demonstrates the utility of this method in organic synthesis