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 |