Diastereoselectivity in the Lateral Metalation and Electrophilic Quenching of Isoxazolyloxazolines

Yousef R. Mirzaei, Brenda Mallet Simpson, David J. Triggle, Nicholas R. Natale

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Metalation and electrophilic quenching of chiral isoxazolyloxazolinee at the C-5 position of the isoxazole gives rise to modest diastereoselectivity in most cases. In general, the 4(S)-(methoxymethyl)-5(S)-phenyl-2-oxazoline auxilliary (Meyer's reagent) produces the S absolute configuration at the C-5 isoxazole position of the major diastereomer, for priorities isoxazole > El > R > H. The enantiomerically pure isoxazolyloxazolines 3 can be obtained by preparative HPLC. The isoxazolyloxazolines 3 can be deprotected selectively to produce isoxazolecarboxaldehyde 4, and 4-isoxazolyl-1,4-dihydropyridine 5. The solid-state conformation of 5 is O-endo with respect to the ring juncture between the heterocyclic rings and sp, sp with respect to the 3,5-diester groups. The (+) enantiomer of IDHP 5 proved to be 2 orders of magnitude more effective in the displacement of 3H-labeled 1,4-dihydropyridine from Ca2+ channels in cardiac membranes.

Original languageEnglish
Pages (from-to)6271-6279
Number of pages9
JournalJournal of Organic Chemistry
Issue number23
StatePublished - Nov 1 1992


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