@Article{AngewChemIntlEd_54_7520, author = {S.A. Pujari and C. Besnard and T. B{\"u}rgi and J. Lacour}, title = {{A Mild and Efficient CH$_2$-Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases}}, journal= {Angew. Chem. Intl. Ed.}, ISSN = {1433-7851}, volume= {54}, number= {26}, pages = {7520-7523}, url = {http://doi.wiley.com/10.1002/anie.201500435}, eprint= {http://www.unige.ch/sciences/chifi/publis/refs_pdf/ref01472.pdf}, doi= {10.1002/anie.201500435}, keywords= {configuration determination;enantioselectivity;heterocycles;ring contraction;stereochemistry}, abstract = {{A novel CH$_2$-extrusion reaction leading to the transformation of ethano-Tröger bases into disubstituted methano derivatives is reported (yields up to 93 %). Under mild and metal-free oxidative conditions, a loss of CH$_2$ and a ring contraction are provoked. Despite two bond cleavages at stereogenic nitrogen and carbon centers and a temporary rupture of the bicyclic structure, a very high enantiospecificity (es≥98 %) is observed for this unusual reaction.}}, year = {2015} }