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Organocatalytic Direct Enantioselective Hydrophosphonylation of N‑Unsubstituted Ketimines for the Synthesis of α‑Aminophosphonates

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posted on 2023-02-17, 12:35 authored by Koki Yamada, Yuta Kondo, Akihiko Kitamura, Tetsuya Kadota, Hiroyuki Morimoto, Takashi Ohshima
We report an organocatalyzed direct enantioselective hydrophosphonylation of N-unsubstituted ketimines that affords N-unprotected α-tetrasubstituted α-aminophosphonates without protection/deprotection steps. The reaction is suitable for N-unsubstituted isatin-derived and trifluoromethyl ketimines, affording products in high yields with excellent enantioselectivity. Applications of the reaction and a proposed transition state model are also described.

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