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Asymmetric and nonasymmetric addition of RLi and RMgX to 3-methoxynaphthalen-2-yl oxazolines and imines. An approach to substituted 2-tetralones
- Source :
- The Journal of organic chemistry. 65(10)
- Publication Year :
- 2000
-
Abstract
- Chiral and achiral 3-methoxynaphthalen-2-yl oxazolines 4a,b failed to undergo an aromatic nucleophilic displacement of the 3-methoxy group with organolithium reagents and instead afforded dihydronaphthalenes 9 and 14 in 30-95% yield. Dihydronaphthalenes 9 (racemic) and 14 (nonracemic) were easily converted into the corresponding aldehydes 15. Alternatively, aldehydes 15 were prepared via tandem addition of Grignard reagents to imines 17 in 50-65% yield. Aldehydes 15 served as precursors to 3,3, 4-trisubstituted 2-tetralones 16. Use of methyl chloroformate to trap the azaenolate derived from 17f and i-PrMgCl afforded, in 65% yield, a versatile synthetic intermediate 23 which may serve to access 4-alkyl-, 3,4-dialkyl-, 3,4-disubstituted and 3,3, 4-trisubstituted 2-tetralones with diverse substitution patterns.
Details
- ISSN :
- 15206904
- Volume :
- 65
- Issue :
- 10
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....7461c85818ad750696ed98cf5f7ab4c5