Abstract
The extended cyclic enolate derived from a simple pyrrol-3-en-2-one (butenolactam) was deuterated at the 5-position with very high diastereoselectivity if the nitrogen atom carries an α-methyl-p- methoxybenzyl group. A similar diastereoselective protonation was observed in a pyrrol-3-en-2-one formed by dearomatising cyclisation of a pyrrole. Protonation of an N-α-methyl-p-methoxybenzyl dihydroisoindolone lacked stereoselectivity.
| Original language | English |
|---|---|
| Pages (from-to) | 2235-2241 |
| Number of pages | 7 |
| Journal | Tetrahedron: Asymmetry |
| Volume | 16 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - 4 Jul 2005 |
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Clayden, J., Turnbull, R., & Pinto, I. (2005). Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: An attempted 'de-epimerisation'. Tetrahedron: Asymmetry, 16(13), 2235-2241. https://doi.org/10.1016/j.tetasy.2005.05.042