367939-65-9Relevant academic research and scientific papers
Chiral aminoalcohols with a menthane skeleton as catalysts for the enantioselective addition of diethylzinc to benzaldehyde
Panev, Stefan,Linden, Anthony,Dimitrov, Vladimir
, p. 1313 - 1321 (2001)
Novel chiral aminoalcohols were synthesized by highly diastereoselective addition of Me3SiCN and LiCH2CN to (-)-menthone followed by LiAlH4 reduction. The addition of CH2=CH-MgBr and PhCH=CH-MgBr to menthone and the following epoxidation, provided useful hydroxy epoxides, one of which could be aminolyzed to afford an aminodiol. In one case, the configuration of the newly formed epoxidic stereogenic center was determined by X-ray crystallography. When applied as catalysts in the enantioselective addition of Et2Zn to benzaldehyde, the aminoalcohols induced enantiomeric excesses (e.e.s) of up to 77%.
