A convenient preparation of (1 R,2S,3R,4S)-3-(neopentyloxy)isoborneol (= (1 R,2S,3R,4S)-3-(2,2-dimethylpropoxy)-I ,7,7-trimethylbicyclo[2.2.l]heptan-2-ol; la), a valuable chirdl auxiliary, is described. The synthesis iiivolves six steps starting from the readily available camphorquinone ( 5 ) and gives l a in 48% overall yield. The key step is the chemoselective hydrolysis of the less hindered 3,3-dioxolane moiety in the camphorquinone diacetal 4.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.