Diastereoselective Access to cis‐1,4‐Disubstitued Tetrahydro‐γ‐carbolines via a [Cp*RhCl₂]₂‐Catalyzed Formal [3+3]‐Cycloaddition

Abstract

A [Cp*RhCl2]2‐catalyzed formal [3+3]‐cycloaddition involving sequential ring opening of aziridines initiated by C−H activation and Michael addition has been developed for the construction of cis‐1,4‐disubstitued tetrahydro‐γ‐carbolines. The advantages of this strategy include broad substrate scope, excellent cis‐diastereoselectivities, highly functionalized products, and mild conditions.

Recent advances in the accessibility, synthetic utility, and biological applications of aziridines

“…The resulting intermediate 311 undergoes Michael addition to form a six-membered ring (Scheme 55). 89 According to the authors, only the formations of the cis -1,4-diastereomers was observed.…”