Abstract
The diastereoselective glyoxylate-ene reaction of N-glyoxyloyl camphorpyrazolidinone (1) with various alkenes 2a-g in the presence of Lewis acid is described. The corresponding α-hydroxyl carbonyls were generally obtained in moderate to high chemical yields (64-87%) and with high levels of diastereoselectivities (up to 94% de). The predominance of products with the S absolute configuration at the newly formed stereogenic center was established by single crystal X-ray analysis and the importance of stereochemical induction is discussed.
| Original language | English |
|---|---|
| Pages (from-to) | 9345-9347 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 45 |
| Issue number | 51 |
| DOIs | |
| Publication status | Published - 2004 Dec 13 |
Keywords
- Diastereoselective
- Glyoxylate-ene reaction
- Stereogenic center
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Pan, J. F., Venkatesham, U., & Chen, K. (2004). An efficient diastereoselective glyoxylate-ene reaction using N-glyoxyloyl camphorpyrazolidinone as an enophile. Tetrahedron Letters, 45(51), 9345-9347. https://doi.org/10.1016/j.tetlet.2004.10.121