115401-41-7Relevant academic research and scientific papers
Copper(I) mediated highly diastereoselective conjugate addition of Grignard reagents to functionalised cycloalkenols: A general and efficient route for the stereoselective synthesis of 5- and 6-membered ring trisubstituted cycloalkanols
Dambrin, Valéry,Villiéras, Monique,Janvier, Pascal,Toupet, Lo?c,Amri, Hassen,Lebreton, Jacques,Villiéras, Jean
, p. 2155 - 2170 (2007/10/03)
The conjugate addition of magnesium cuprates to various 2-silyloxycyclopentene and 2-silyloxycyclohexene carboxylates leads diastereoselectively to related syn-anti cyclopentanols and cyclohexanols in fair overall yields. The β-elimination occurring with free hydroxylic derivatives is also partially or totally avoided by concomitant in situ trapping of the generated enolates. Attempts to rationalise our results are discussed.
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.
