Back to Search
Start Over
N-Chloroformylimidazolidinone Enolates as 1,3-Dipolar Reagents for the Stereoselective Synthesis of 3,4-Dihydroisoquinolones
- Source :
- Organic Letters; March 2019, Vol. 21 Issue: 6 p1908-1911, 4p
- Publication Year :
- 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 (AlCl3) 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.
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Volume :
- 21
- Issue :
- 6
- Database :
- Supplemental Index
- Journal :
- Organic Letters
- Publication Type :
- Periodical
- Accession number :
- ejs48672360
- Full Text :
- https://doi.org/10.1021/acs.orglett.9b00548