Second Generation Catalytic Asymmetric Synthesis of Tamiflu: Allylic Substitution Route
Organic Letters2006Vol. 9(2), pp. 259–262
Citations Over TimeTop 10% of 2006 papers
Abstract
Catalytic asymmetric synthesis of Tamiflu, an important antiinfluenza drug, was achieved. After the catalytic enantioselective desymmetrization of meso-aziridine 3 with TMSN3, using a Y catalyst (1 mol %) derived from ligand 2, an allylic oxygen function and C1 unit on the C=C double bond were introduced through cyanophosphorylation of enone and allylic substitution with an oxygen nucleophile. This second generation route of Tamiflu is more practical than our previously reported route. [reaction: see text].
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