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Organocatalytic Asymmetric Decarboxylative Mannich Reaction of β‑Keto Acids with Cyclic α‑Ketiminophosphonates: Access to Quaternary α‑Aminophosphonates

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journal contribution
posted on 31.05.2018, 13:46 by Yong-Jie Liu, Jin-Shan Li, Jing Nie, Jun-An Ma
An organocatalytic asymmetric decarboxylative Mannich reaction of β-keto acids with cyclic α-ketiminophosphonates has been developed. By using saccharide-derived bifunctional amine-thiourea catalysts bearing an axial chiral binaphthyl scaffold, a wide range of quaternary α-amino-γ-oxophosphonates were obtained in up to 93% yield and >99% ee. Furthermore, two interesting α-aminophosphonate derivatives were synthesized from the corresponding decarboxylative Mannich product via simple transformations.