Design and Enantioselective Synthesis of β‑Vinyl Tryptamine Building Blocks for Construction of Privileged Chiral Indole Scaffolds

The highly efficient and stereo-specific
synthesis of the enantioenriched
versatile building blocksnamely, β-vinyltryptaminesby
rhodium-catalyzed allylic substitutions of vinylaziridines and indoles
is presented. Besides indoles, pyrroles can also serve as competent
carbon nucleophiles in the current reaction, which is different from
the previous works. To demonstrate the synthetic utility of our method,
up to 11 natural product and pharmaceutically relevant chiral indole
scaffolds were synthesized in highly efficient reaction sequences.
Notably, asymmetric formal synthesis of a potent constrained analogue
of MS-245 and a nNOS and 5-HT1B/1D receptor inhibitor are
also reported.