Practical asymmetric synthesis of bioactive aminotetralins from a racemic precursor using a regiodivergent resolution.
Catalyst-controlled asymmetric ring opening of a racemic oxabicyclic alkene leads to two readily separable regioisomeric products both in excellent ee. A cationic Rh catalyst, with added NH(4)BF(4) to modulate reactivity, was required to obtain synthetically useful yields. The utility of each substituted aminotetralin product has been demonstrated by their conversion to different biologically relevant molecules in a highly efficient and practical manner.
Department of Chemistry, University of Toronto, Toronto, Ontario, Canada, M5S 3H6.
Robert
R
Webster
Alistair
A
Boyer
Matthew J
MJ
Fleming
Mark
M
Lautens
D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis*
D013764:Tetrahydronaphthalenes