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N-Chloroformylimidazolidinone Enolates as 1,3-Dipolar Reagents for the Stereoselective Synthesis of 3,4-Dihydroisoquinolones

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)1908-1911
Number of pages4
JournalOrganic Letters
Issue number6
Early online date25 Feb 2019
DateAccepted/In press - 25 Feb 2019
DateE-pub ahead of print - 25 Feb 2019
DatePublished (current) - 15 Mar 2019


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.



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