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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).