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Metal Template Assisted Proximal Arrangement of a Nucleophile and an Electrophile: Site-Selective Acylation of α-Hydroxyamides in Polyols

2018; American Chemical Society; Volume: 20; Issue: 11 Linguagem: Inglês

10.1021/acs.orglett.8b01288

1523-7060

Yasuhiro Nishikawa, Kohei Takemoto, Kana Matsuda, Tanaka Risa, Akira Arashima, Kanako Ito, Yuki Kamezawa, Yuna Hori, Osamu Hara,

Asymmetric Synthesis and Catalysis

Site-selective acylation of α-hydroxyl groups in amides has been achieved in the presence of other primary hydroxyl groups with intrinsic high reactivity. In this methodology, a relatively stable pyridine aldoxime ester was exploited as an acyl donor to suppress undesired acylation. The catalytic activation of a pyridine aldoxime ester with a Lewis acid produced a cationic complex, which preferentially attracted the Lewis basic α-hydroxyamide via a template effect, to thus facilitate o-acylation.