Combined organo- and gold-catalyzed enantioselective synthesis of bicyclic enones

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 -