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Complementary diastereoselectivity in the intermolecular addition of titanium and magnesium naphtholates to asymmetric lactaldehydes

Giles, R.G.F., Joll, C.A., Sargent, M.V. and Tilbrook, D.M.G. (1999) 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.

Link to Published Version: http://dx.doi.org/10.1039/A901456J
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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.

Publication Type: Journal Article
Murdoch Affiliation: School of Mathematical and Physical Sciences
Publisher: Royal Society of Chemistry
Copyright: © 1999 Royal Society of Chemistry
URI: http://researchrepository.murdoch.edu.au/id/eprint/35538
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