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 |
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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