910057-84-0Relevant academic research and scientific papers
Modular and stereoselective synthesis of tetrasubstituted helical alkenes via a palladium-catalyzed domino reaction
Liu, Hongqiang,El-Salfiti, Mohamed,Chai, David I.,Auffret, Jeremy,Lautens, Mark
supporting information; experimental part, p. 3648 - 3651 (2012/09/08)
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.
Total synthesis of jimenezin via an intramolecular allylboration
Bandur, Nina G.,Brueckner, David,Hoffmann, Reinhard W.,Koert, Ulrich
, p. 3829 - 3831 (2007/10/03)
An efficient total synthesis of the annonaceous acetogenin jimenezin was achieved. The key steps used were a highly stereoselective intramolecular allylboration to establish the tetrahydropyran ring and an intramolecular Williamson reaction to close the tetrahydrofuran ring.
