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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
DDQ-Promoted Benzylic/Allylic sp(3) C-H Activation for the Stereoselective Intramolecular C-N Bond Formation:
Macha Lingamurthy1, Yerri Jagadeesh1, Katakam Ramakrishna1
1Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology , Tarnaka, Hyderabad, 500007 Telangana, India.
Abstract:
This is the first report on an intramolecular C-N bond formation of an amide-tethered benzylic/allylic system using DDQ under neutral conditions which has been successfully applied to the total synthesis of naturally occurring pyrolidine alkaloids. The key steps for the synthesis of corresponding precursors involve Julia-Kociensky olefination/cross-metathesis and dihydroxylation reactions, and this methodology is also extended to the ω-unsaturated N-sulfanilamide to furnish piperidines.
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