Related Experiment Video
Updated: Jul 17, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Second generation catalytic asymmetric synthesis of Tamiflu: allylic substitution route
Tsuyoshi Mita1, Nobuhisa Fukuda, Francesc X Roca
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
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].
More Related Videos
Related Concept Videos
Radical Substitution: Allylic Bromination
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition
Radical Substitution: Allylic Chlorination
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

