H. Suga, Hiroki Fujieda, Y. Hirotsu
Jun 1, 1994
Citations
0
Influential Citations
14
Citations
Journal
Journal of Organic Chemistry
Abstract
The formal [3+2] cycloaddition of 5-methoxy-2-(p-methoxyphenyl)oxazole with 2(S)-(benzyloxy)-propanal and 2(S)- [(tert-butyldimethylsilyl)- oxy]propanal in the presence of tin(IV) chloride gave cis-(4R,5S,1'S)- and trans-(4S,5S,1'S)-5-(1'-alkoxyethyl)-4-(methoxycarbonyl)-2-(p-me- thoxyphenyl)-2-oxazolines with high diastereoselectivity (94 and 92% selectivity, respectively). A similar reaction of 5-methoxy-2-(p-metho- xyphenyl)oxazole with 2,3-di-O-benzyl-D-glyceraldehyde gave methyl cis- (4S,5R,1'R)-2-(p-methoxyphenyl)-5-[1',2'-bis(benzyloxy)ethyl]-2-oxazo- line-4-carboxylate with high diastereoselectivity (>95% selectivity), and the latter was easily converted to biologically important chiral 2-amino-1,3,4,5-tetrol derivatives