%0 Journal Article %A Liu, Hongqiang %A El-Salfiti, Mohamed %A Chai, David I. %A Auffret, Jérémy %A Lautens, Mark %D 2012 %T Modular and Stereoselective Synthesis of Tetrasubstituted Helical Alkenes via a Palladium-Catalyzed Domino Reaction %U https://acs.figshare.com/articles/journal_contribution/Modular_and_Stereoselective_Synthesis_of_Tetrasubstituted_Helical_Alkenes_via_a_Palladium_Catalyzed_Domino_Reaction/2503621 %R 10.1021/ol301495q.s003 %2 https://acs.figshare.com/ndownloader/files/4146547 %K chiral helical alkenes %K alkene formation %K homologative alkynylation %K stereoselective synthesis %K enantiopure bromoalkyl aryl alkyne precursors %K protocol features %K helical diastereoselectivity %K tetrasubstituted helical alkenes %K norbornene incorporation %K Tetrasubstituted Helical Alkenes %K Stereoselective Synthesis %X A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C–C bonds via sequential C–H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation. %I ACS Publications