p-Menthane-3-carboxaldehyde: a useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity
Journal of the American Chemical Society
(+)- 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 ?-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.
Spino, Claude, Cédrickx Godbout, Christian Beaulieu, Magali Harter, Topwe M. Mwene-Mbeja, and Luc Boisvert. "P-menthane-3-carboxaldehyde: a Useful Chiral Auxiliary for the Synthesis of Chiral Quaternary Carbons of High Enantiomeric Purity." Journal of the American Chemical Society. 126.41 (2004): 13312-13319. Print.