Abstract
Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3999-4002 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 8 |
| Issue number | 18 |
| DOIs | |
| State | Published - Aug 31 2006 |
| Externally published | Yes |
ASJC Scopus subject areas
- Molecular Medicine
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Ng, P. Y., Masse, C. E., & Shaw, J. T. (2006). Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: Synthesis of the tricyclic core of martinellic acid. Organic Letters, 8(18), 3999-4002. https://doi.org/10.1021/ol061473z