61449-06-7Relevant academic research and scientific papers
Regiospecific control of additions of 4-substituted 3,5-dimethylisoxazoles to α,β unsaturated carbonyls
Stenzel,Natale
, p. 1041 - 1044 (1997)
Transmetalation of C-5-lithiomethylisoxazoles with the lower-order cuprate reagent lithium thienylcyanocuprate (Li[ThCuCN]) in THF results in exclusive conjugate addition to α,β-unsaturated carbonyls. In contrast, transmetalation with samarium tris(hexamethyldisilazide) (Sm[HMDS]3) in diethyl ether directs 1,2-carbonyl addition. In both cases, optimum results were realized with a 4,5-dihydro-4,4-dimethyl-Δ2-2-oxazoline substituent at the C-4 position of the isoxazole.
