H. Pajouhesh, K. Curry
Aug 21, 1998
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Influential Citations
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Isoxazole amino acids are an important class of neuroexcitant which are difficult to prepare in enantiopure form. Diastereoselective alkylation of the enantiomerically pure glycine derivative, tert-butoxycarbonyl-2-(tert-butyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate (Boc-BMI) with 4-bromomethyl-2-methoxymethyl-5-methylisoxazolin-5-one 5 or 5-bromomethyl-4-bromo-3-methoxyisoxazole, gives intermediates which under mild hydrolysis conditions produce the amino acids ( S )- and ( R )-bromohomoibotenic acid and ( S )- and ( R )-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid with e.e. >99%.