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Asymmetric Alkenyl C-H Functionalization by Cpx RhIII forms 2H-Pyrrol-2-ones through [4+1]-Annulation of Acryl Amides and Allenes.

Shou-Guo WangYang LiuNicolai Cramer
Published in: Angewandte Chemie (International ed. in English) (2019)
An efficient Cpx RhIII -catalyzed enantioselective alkenyl C-H functionalization/[4+1] annulation of acryl amides and allenes is reported. The described transformation provides straightforward access to enantioenriched α,β-unsaturated-γ-lactams bearing a quaternary stereocenter. The reaction operates under mild conditions, displays a broad functional-group tolerance, and provides 2H-pyrrol-2-ones with excellent selectivity of up to 97:3 er. Such scaffolds are frequently found in natural products and synthetic bioactive compounds and are of significant synthetic value. It is noteworthy that the allene serves as a one-carbon unit in the [4+1]-annulation.
Keyphrases
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