Skip to content

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
Volume21
Issue number6
Early online date25 Feb 2019
DOIs
DateAccepted/In press - 25 Feb 2019
DateE-pub ahead of print - 25 Feb 2019
DatePublished (current) - 15 Mar 2019

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.

Documents

Documents

  • Full-text PDF (accepted author manuscript)

    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at https://pubs.acs.org/doi/10.1021/acs.orglett.9b00548 . Please refer to any applicable terms of use of the publisher.

    Accepted author manuscript, 840 KB, PDF-document

    Embargo ends: 25/02/20

    Request copy

DOI

View research connections

Related faculties, schools or groups