Abstract
N-Chloroformyl imidazolidinone derivatives of enantiopure amino acids may be deprotonated to give remarkably well-behaved enolates with both nucleophilic and electrophilic character. The enolates undergo diastereoselective C-alkylation with benzylic halides. A Bischler-Napieralski-like cyclization reaction onto the chloroformyl group, induced by either nucleophilic (KI, 2,6-lutidine) or Lewis acid (AlCl 3 ) catalysis, gives substituted 3,4-dihydroisoquinolone derivatives in enantioenriched form. The reaction sequence constitutes a formal [3 + 3] route to the six-membered lactam ring of the dihydroisoquinolones.
Original language | English |
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Pages (from-to) | 1908-1911 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 21 |
Issue number | 6 |
Early online date | 25 Feb 2019 |
DOIs | |
Publication status | Published - 15 Mar 2019 |