TY - JOUR
T1 - Combined organo- and gold-catalyzed enantioselective synthesis of bicyclic enones
AU - Zweifel, Theo
AU - Hollmann, Dirk
AU - Prüger, Birgit
AU - Nielsen, Martin
AU - Jørgensen, Karl Anker
PY - 2010/6/23
Y1 - 2010/6/23
N2 - By combining organocatalysis with gold catalysis highly enantioenriched bicyclic enones are available via an operationally simple one-pot procedure. Iminium-ion activation by cinchona alkaloid-derived primary amine catalysts induces the Michael addition of propargylated malononitriles and cyanoacetates to α,β-unsaturated ketones. The resulting intermediates undergo an exo-dig cyclization, forming a new C-C bond followed by double-bond isomerization to give highly functionalized bicyclic enones in good yields and high enantioselectivities.
AB - By combining organocatalysis with gold catalysis highly enantioenriched bicyclic enones are available via an operationally simple one-pot procedure. Iminium-ion activation by cinchona alkaloid-derived primary amine catalysts induces the Michael addition of propargylated malononitriles and cyanoacetates to α,β-unsaturated ketones. The resulting intermediates undergo an exo-dig cyclization, forming a new C-C bond followed by double-bond isomerization to give highly functionalized bicyclic enones in good yields and high enantioselectivities.
UR - http://www.scopus.com/inward/record.url?scp=77956649664&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2010.05.044
DO - 10.1016/j.tetasy.2010.05.044
M3 - Journal article
AN - SCOPUS:77956649664
SN - 0957-4166
VL - 21
SP - 1624
EP - 1629
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 11-12
ER -