- A Mild and Efficient CH2-Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases
Sandip A. Pujari, Céline Besnard, Thomas Bürgi, Jérôme Lacour
Angew. Chem. Int. Ed. 2015, 54, 7520-7523
A novel CH2-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 CH2 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.
open archive unige:73259