Regiospecific control of additions of 4-substituted 3,5-dimethylisoxazoles to α,β unsaturated carbonyls

J. R. Stenzel, N. R. Natale

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)1041-1044
Number of pages4
JournalSynthesis (Germany)
Issue number9
DOIs
StatePublished - 1997

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