An asymmetric isoxazole annulation

Brian E. Marron, Ludwig Schlicksupp, N. R. Natale

Research output: Contribution to journalArticlepeer-review

Abstract

An Asymmetric isoxazole annulation proceeds from the (S)‐O‐methoxyphenylalaninol imine of (RS)‐2‐phen‐ylpropionaldehyde (3). Deprotonation, quenching with 4‐chloromethyl‐3,5‐dimethylisoxazole, and hydrolysis produced isoxazolylaldehyde (5), whose structure was confirmed by single crystal X‐ray diffractometry. The absolute configuration of (‐)‐5 was established as (R)‐by chemical correlation to the known (S)‐(‐)‐4‐methyl‐4‐phenyl‐cyclohex‐2‐ene‐1‐one (7).

Original languageEnglish
Pages (from-to)1067-1070
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume25
Issue number4
DOIs
StatePublished - 1988

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