Photoinduced Lactamization/Truce-Smiles Rearrangement Cascade Enables Access to Lactam-Fused β-Arylethylamines
Panyi Huang1, Yixuan Tang1, Xinyu Li2
1Institute of Advanced Studies and School of Pharmaceutical Sciences, Taizhou University, Jiaojiang 318000, P. R. China.
Abstract:
The radical Truce-Smiles rearrangement (TSR) is a powerful and step-economical 1,4-aryl migration strategy that enables the direct synthesis of high-value β-arylethylamine pharmacophore from simple materials. Herein, we report the diastereoselective synthesis of lactam-fused arylethylamines from a linear sulfonamide substrate through an intramolecular lactamization/TSR rearrangement cascade. The stereochemical outcome is governed by a rigid cyclic transition state. Furthermore, driven by an electron donor-acceptor (EDA) complex under metal- and photocatalyst-free conditions, this cascade proceeds via two consecutive 5-exo-trig cyclizations, exhibiting excellent diastereoselectivity and functional group compatibility.
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