94035-65-1Relevant academic research and scientific papers
Complementary diastereoselectivity in the intermolecular addition of titanium and magnesium naphtholates to asymmetric lactaldehydes
Giles, Robin G. F.,Joll, Cynthia A.,Sargent, Melvyn V.,Tilbrook, D. Matthew G.
, p. 3029 - 3038 (2007/10/03)
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 (15, 2R, 1″R or S)-1-(7′-benzyloxy-4′,5′-dimethoxy-1′-hydroxy-2′- naphthyl)-2-(1″-ethoxyethoxy)propan-l-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. The Royal Society of Chemistry 1999.
