130252-08-3Relevant articles and documents
SUBSTITUTION NUCLEOPHILE D'ACETATES DE CYCLENOLS ALLYLIQUES FONCTIONNELS PAR DES ORGANOMETALLIQUES EN PRESENCE DE SELS CUIVREUX. APPLICATION A UNE SYNTHESE RAPIDE DE LA (+/-) MITSUGASHIWALACTONE
Amri, Hassen,Rambaud, Monoque,Villieras, Jean
, p. 3535 - 3546 (2007/10/02)
Substitution of functional allylic cycloalkenol acetates by Grignard reagents (primary, secondary, tertiary-alkyl, vinyl, aryl) in the presence of a catalytic amount (2.5percent equivalent) of cuprous iodide at low temperature, gives high yields of various functional α-substituted cycloalkenes.The reaction can be applied to lithium enolates of esters and need no catalyst, but may be performed with HMPA as cosolvent.It is illustrated by a short (6 steps) and efficient total selective synthesis of (+/-)-mitsugashiwalactone from 2,5-dimethoxytetrahydrofuran with 33percent overall yield.