Abstract
The nitrones derived from β-allyloxyaldehydes with a β-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a γ-allyloxyaldehyde with a γ-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose.
| Original language | English |
|---|---|
| Pages (from-to) | 1323-1340 |
| Number of pages | 18 |
| Journal | Tetrahedron Asymmetry |
| Volume | 7 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 1996 May |
ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
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Shing, T. K. M., Wong, C. H., & Yip, T. (1996). Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy. Tetrahedron Asymmetry, 7(5), 1323-1340. https://doi.org/10.1016/0957-4166(96)00149-8