The Journal of Organic Chemistry

3-Unsubstituted 1, 5-Diaryl-2, 4-pentanediones and-4-methoxy-2-pentanones: Synthesis via Corresponding 3-Hydroxy Ketones Generated from 2-Isoxazolines

JT Pulkkinen, JJ Vepsäläinen

Index: Pulkkinen, Juha T.; Vepsaelaeinen, Jouko J. Journal of Organic Chemistry, 1996 , vol. 61, # 24 p. 8604 - 8609

Full Text: HTML

Citation Number: 28

Abstract

Aryl acetaldoximes are reacted with allylarenes in the presence of sodium hypochlorite to give 3, 5-bis (arylmethyl)-2-isoxazolines which are then converted to 1, 5-diaryl-4-hydroxy-2- pentanones by a reductive hydrogenation in the presence of water. These intermediate aldols can then be either oxidized with Corey-Kim reagent to stable dimethylsulfonium 1- (arylacetyl)-2-oxo-3-arylpropylides followed by zinc-acetic acid reduction to give 1, 5- ...