Synlett 2003(4): 0567-0569
DOI: 10.1055/s-2003-37526
LETTER
© Georg Thieme Verlag Stuttgart · New York

O-Allylic Substitution of Hydroxylamine Derivatives Having an N-Electron-Withdrawing Substituent

Hideto Miyabea, Kazumasa Yoshidaa, Akira Matsumuraa, Masashige Yamauchib, Yoshiji Takemoto*a
a Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
Fax: +81(75)7534569; e-Mail: takemoto@pharm.kyoto-u.ac.jp;
b Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-0295, Japan
Further Information

Publication History

Received 27 January 2003
Publication Date:
26 February 2003 (online)

Abstract

The O-allylic substitution of hydroxylamines having an N-electron-withdrawing substituent proceeded smoothly to afford O-allylated products by using [IrCl(cod)]2 or Pd(PPh3)4.

9

The cyclic products 14c-e were obtained as a diastereomeric mixture in about 10:1 ratio by 1H NMR, although these stereochemistries have not be determined.