Lewis Acid Catalyzed Domino Generation/[2,3]-Sigmatropic Rearrangement of Ammonium Ylides to Access Chiral Azabicycles
Min Zhang and Yu Lan report on a Lewis acid catalyzed synthesis of chiral azybicycles.
The N-fused azabicycle with a bridgehead quaternary center in fused 5/X (X = 5, 6, 7) rings is one of the most ubiquitous bicyclic structural frameworks. This motif is also the central structural unit found in a large number of therapeutics and natural products. Professor Min Zhang from Chongqing University (P. R. of China), whose group has a long-standing interest in the total synthesis of complex natural products, explained that – from the chemistry viewpoint – the development of efficient reactions to construct such bicyclic ring systems remains a daunting challenge for organic chemists, presumably because of the problems associated with quaternary stereogenic center installment, as well as the inefficiency of bicyclic framework construction.
On the project described in the article Professor Zhang’s group collaborated with the group of Professor Yu Lan from the same university.