H. Pajouhesh, Mahmonir Hosseini-Meresht, Seyed Hossein Pajouhesh
Dec 15, 2000
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract The preparation of both enantiomers of 2-amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl) propanoic acid (ATPA), 1 , an analogue of the neuroexcitant 2-amino-3-(3-hydroxy-5-methyl-4-yl) propanoic acid (AMPA) is described. The enantiomerically pure glycine derivative tert- butoxycarbonyl-2-( tert- butyl)-3-methyl-4-oxo-1-imidazolidinecarboxylate (BOC-BMI) was coupled with 4-bromomethyl-2-methoxymethyl-5- tert- butylisoxazolin-3-one 6 to give the intermediates (2 R ,5 R )- 8 and (2 S ,5 S )- 8 . These alkylated products were hydrolyzed under mild conditions to give enantiopure ( R )- 1 and ( S )- 1 with e.e.'s in excess of 99% in 33% overall yield.