Tetrahedron: Asymmetry

An efficient and general enantioselective synthesis of some isoxazole-containing analogues of the neuroexcitant glutamic acid

H Pajouhesh, K Curry

Index: Pajouhesh, Hassan; Curry, Kenneth Tetrahedron Asymmetry, 1998 , vol. 9, # 16 p. 2757 - 2760

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Citation Number: 7

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 ...