An asymmetric isoxazole annulation | Zendy

Marron Brian E. | Zendy; Schlicksupp Ludwig | Zendy; Natale N. R. | Zendy

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An asymmetric isoxazole annulation

Author(s) -

Marron Brian E.,

Schlicksupp Ludwig,

Natale N. R.

Publication year - 1988

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570250404

Subject(s) - chemistry , isoxazole , annulation , imine , deprotonation , absolute configuration , medicinal chemistry , quenching (fluorescence) , stereochemistry , organic chemistry , catalysis , fluorescence , ion , physics , quantum mechanics

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).

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