UNIGE document Scientific Article
previous document  unige:11037  next document
add to browser collection

Enantioselective iminium-catalyzed epoxidation of hindered trisubstituted allylic alcohols

Published in Tetrahedron: Asymmetry. 2010, vol. 21, no. 11-12, p. 1611 - 1618
Abstract The reactivity of diastereomeric biaryl iminium cations made of a (Ra)-5,5',6,6',7,7',8,8'-octahydrobinaphthyl core and exocyclic appendages derived from (S)- or (R)-3,3-dimethylbutyl-2-amine was investigated with hindered trisubstituted allylic alcohols—a class of alkenes which had not been previously studied in detail in epoxidation reactions with cyclic iminium catalysts (ee up to 98%). Surprisingly, generally strong matched/mismatched effects are observed not only in terms of reactivity but also on the enantioselectivity of the reaction (Δee up to 16%). Also, for the most hindered substrates, two sets of reaction conditions were tested in a preliminary study and little advantage was found in running reactions in MeCN/water instead of CH2Cl2/water/18-C-6. In any case, the presence of the hydroxyl group did not reveal any anchimeric effect.
Full text
(ISO format)
NOVIKOV, Roman, LACOUR, Jérôme. Enantioselective iminium-catalyzed epoxidation of hindered trisubstituted allylic alcohols. In: Tetrahedron: Asymmetry, 2010, vol. 21, n° 11-12, p. 1611 - 1618. https://archive-ouverte.unige.ch/unige:11037

172 hits

0 download


Deposited on : 2010-08-27

Export document
Format :
Citation style :