Tetrahedron letters

An acyliminium ion approach towards the synthesis of β-substituted 3, 4-dihydroisoquinolone propionates

MJ Fisher, BP Gunn, S Um, JA Jakubowski

Index: Fisher, Matthew J.; Gunn, Bruce P.; Um, Suzane; Jakubowski, Joseph A. Tetrahedron Letters, 1997 , vol. 38, # 33 p. 5747 - 5750

Full Text: HTML

Citation Number: 8

Abstract

A variety of α-methoxy amides were prepared either by selective reduction of the exocyclic carbonyl of a 2-acyl-3, 4-dihydroisoquinolone and subsequent trapping of the resultant α- hydroxy amide with acidic methanol or by reacting the sodium salt of 3, 4- dihydroisoquinolone with a functionalized α-chloro ether. These intermediates were reacted with 1-tert-butoxy-1-tert-butyldimethylsiloxy ethene in the presence of BF3· Et2O providing ...