Journal article
Complementary diastereoselectivity in the intermolecular addition of titanium and magnesium naphtholates to asymmetric lactaldehydes
Journal of the Chemical Society, Perkin Transactions 1, (20), pp.3029-3038
1999
Abstract
Addition of 7-benzyloxy-4,5-dimethoxy-1-naphthol 3 as its triisopropoxytitanium naphtholate to (2R, 1′R or S )-2-(1′-ethoxyethoxy)propanal 4 afforded solely (1S, 2R, 1″R or S )-1-(7′-benzyloxy-4′,5′-dimethoxy-1′-hydroxy-2′-naphthyl)-2-(1″-ethoxyethoxy)propan-1-ol 5, being the erythro product arising from anti addition. Complementary reaction of the naphthol 3 as its bromomagnesium naphtholate with aldehyde 4 gave rise solely to the alternative (1R, 2R, 1″R or S ) diastereomer 6 . The naphthol 3 was prepared through the completely regioselective addition of 2-methoxyfuran 9 to 5-benzyloxy-3-methoxydehydrobenzene 8. This differentially protected bisalkoxybenzyne was conveniently prepared from vanillin.
Details
- Title
- Complementary diastereoselectivity in the intermolecular addition of titanium and magnesium naphtholates to asymmetric lactaldehydes
- Authors/Creators
- R.G.F. Giles (Author/Creator)C.A. Joll (Author/Creator)M.V. Sargent (Author/Creator) - German Federal ChancelleryD.M.G. Tilbrook (Author/Creator) - School of Medicine and Pharmacology
- Publication Details
- Journal of the Chemical Society, Perkin Transactions 1, (20), pp.3029-3038
- Publisher
- Royal Society of Chemistry
- Identifiers
- 991005540512807891
- Copyright
- © 1999 Royal Society of Chemistry
- Murdoch Affiliation
- School of Mathematical and Physical Sciences
- Language
- English
- Resource Type
- Journal article
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