Journal article
A novel titanium tetrachloride-induced rearrangement of an enantiopure 4-naphthyldioxolane. The possible role of titanium in the umpolung of tosyloxy and chlorine
Tetrahedron Letters, Vol.50(46), pp.6361-6363
2009
Abstract
The rearrangement of (2′S,4′R,5′S)-2-(2′,5′-dimethyl-1′,3′-dioxolan-4′-yl)-4,5,7-trimethoxynaphthalen-1-yl 4″-methylbenzenesulfonate with titanium(IV) chloride affords (1R,3S,4R)-10-chloro-6,7,9-trimethoxy-1,3-dimethyl-3,4-dihydro-4-hydroxynaphtho[1,2-c]pyran in good yield. This transformation is characterized by two unusual aromatic substitution reactions in that, in one, tosyloxy is lost and, in the other, aromatic chlorination occurs with titanium(IV) chloride as the source of chlorine.
Details
- Title
- A novel titanium tetrachloride-induced rearrangement of an enantiopure 4-naphthyldioxolane. The possible role of titanium in the umpolung of tosyloxy and chlorine
- Authors/Creators
- R.G.F. Giles (Author/Creator)J.D. McManus (Author/Creator)
- Publication Details
- Tetrahedron Letters, Vol.50(46), pp.6361-6363
- Publisher
- Elsevier BV
- Identifiers
- 991005540499407891
- Copyright
- © 2009 Elsevier Ltd.
- Murdoch Affiliation
- School of Chemical and Mathematical Science
- Language
- English
- Resource Type
- Journal article
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- Citation topics
- 1 Clinical & Life Sciences
- 1.219 Cancer Drugs
- 1.219.1527 Naphthoquinone Derivatives
- Web Of Science research areas
- Chemistry, Organic
- ESI research areas
- Chemistry