Ai-Lian Wang, Yi-Fan Yao, Xu-Gang Zhang,* and Peng-Fei Xu*
https://doi.org/10.1021/acs.orglett.5c04773
ABSTRACT:
Herein, we report a catalyst-free, photosensitized strategy for synthesizing 1,2-amino alcohols. This transformation proceeds via the addition of an α-hydroxymethyl radical to an in situ-generated alkyliminium ion. The α-hydroxymethyl radical is formed by the radical Brook rearrangement of a (trimethylsilyl)- methoxy radical generated from an electron donor-acceptor (EDA) complex between Hantzsch ester and N-((trimethylsilyl)- methoxy)phthalimide. Therefore, this Mannich-type reaction establishes an additive-free, modular, and simple approach for the synthesis of 1,2-amino alcohols.