Tetrahedron Asymmetry p. 2757 - 2760 (1998)
Update date:2022-08-05
Topics:
Pajouhesh, Hassan
Curry, Kenneth
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%.
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