Novel Gold(I)-catalyzed intermolecular addition of carbonyl compounds to enynes

ORGN 28

Mathias Schelwies, mschelwi@ix.urz.uni-heidelberg.de and Guenter Helmchen, en4@ix.urz.uni-heidelberg.de. Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, Heidelberg, 69120, Germany
The study of transition-metal catalyzed cycloisomerization reactions of enynes has led to innovative new reactions in organic synthesis. In this context, cationic Au(I) complexes have found increasing use as homogeneous catalysts and offer access to a variety of complex polycyclic systems. Recently, we have found a novel and suprising Gold(I)-catalyzed intermolecular addition of carbonyl compounds to enynes leading to 2-oxabicyclo-[3.1.0]hexanes in high stereoselectivity. Optimization, scope and mechanistic aspects of the reaction will be discussed.