Abstract
Methyltin trichloride and indium(III) chloride promote ethyl pyruvate addition to cyclic allylic stannanes to produce α-methyl-α-hydroxy esters with excellent threo-diastereoselectivity (92-100% de). These reactions probably proceed via an initial γ-anti transmetallation followed by a metallo-ene cycloaddition involving internal chelation. The resulting esters can be diastereospecifically converted to the corresponding bicyclic bromolactones.
| Original language | English |
|---|---|
| Pages (from-to) | 1640-1644 |
| Number of pages | 5 |
| Journal | Synthesis |
| Volume | 1998 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - Nov 1998 |
| Externally published | Yes |
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Wayan Muderawan, I., Bott, R. C., & Young, D. J. (1998). Chelation controlled addition of ethyl pyruvate to cyclic allylic stannanes: A diastereospecific route to functionalised bicyclic γ-lactones. Synthesis, 1998(11), 1640-1644. https://doi.org/10.1055/s-1998-2196