Abstract
A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.
| Original language | English |
|---|---|
| Pages (from-to) | 781-789 |
| Number of pages | 9 |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2017 Jan 6 |
ASJC Scopus subject areas
- Organic Chemistry
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Yang, S. M., Madhusudhan Reddy, G., Liu, M. H., Wang, T. P., Yu, J. K., & Lin, W. (2017). Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives. Journal of Organic Chemistry, 82(1), 781-789. https://doi.org/10.1021/acs.joc.6b02526