Title

p-Menthane-3-carboxaldehyde: a useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity

Document Type

Article

Publication Date

2004

Publication Title

Journal of the American Chemical Society

Department

Chemistry

Abstract

(+)- 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.

ISSN

0002-7863