Subscribe to RSS
DOI: 10.1055/s-0033-1340693
Synthesis of Tropanes through Asymmetric [3+2] Cycloaddition
Catalytic Enantioselective Synthesis of Functionalized Tropanes Reveals Novel Inhibitors of Hedgehog Signaling.
Angew. Chem. Int. Ed. 2013;
52: 12892-12896
Publication History
Publication Date:
17 February 2014 (online)
Significance
The tropane scaffold defines the structural core of a variety of alkaloids, and general methods for the preparation of tropanes in a stereocontrolled manner are desired. Antonchick, Waldmann, and co-workers report an approach which provides functionalized tropanes with several quaternary or tertiary stereocenters under mild reaction conditions.
#
Comment
The authors employ S-shaped 1,3-fused azomethine ylides in a catalytic enantioselective [3+2] cycloaddition with nitroalkenes. The reaction offers straightforward access to diversely substituted tropanes in high yields and with good enantioselectivities, irrespective of the electronic and the steric nature of the substituents on the nitroalkenes.
#
#