화학공학소재연구정보센터
Journal of the American Chemical Society, Vol.126, No.41, 13312-13319, 2004
p-Menthane-3-carboxaldehyde: A useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity
(+)- or (-)-p-Menthane-3-carboxaldehyde is made in two easy steps from (+)- or (-)-menthone, respectively. This auxiliary allows for the synthesis of carbonyl compounds bearing a a-chiral quaternary carbon. The flexibility, efficiency, and ease of use of the method are demonstrated in a series of examples, which include the total synthesis of (+)-cuparenone as well as a partial synthesis of (-)-cassiol.