CHED 505 |
3+2 cycloadditions on the azomethine ylide derived from substrate 2 to give products 3 have been explored. The substrate 2 was synthesized from 1-tetralone 1 via a 3-step protocol. The Schmidt reaction converts 1-tetralone (1) to an amide. Amide reduction with LiAlH4 generates amine, followed by amine alkylation forming 2. NBS oxidation of 2 generates an iminium ion, which upon treatment with base generates an azomethine ylide dipole. Cycloadditions with achiral or chiral enoyl oxazolidinones (4) were explored using unsaturated alkene 4 and analogs. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Chemical Education |