Reaction of. alpha.-diketones with 2-amino alcohols. Intramolecular competitive 6-exo-trig vs 5-endo-trig processes. A systematic and kinetic study

…, J Plumet, IM Rodriguez-Campos…

Index: Alcaide, Benito; Plumet, Joaquin; Rodriguez-Campos, Ignacio M. Journal of Organic Chemistry, 1992 , vol. 57, # 8 p. 2446 - 2454

Full Text: HTML

Citation Number: 21

Abstract

2-Aminoethanol and C-substituted derivatives 1 react with diacetyl, benzil, and l-phenyl-l, 2- propanedione, models of a-diketones 2 to give with remarkable regie and stereoselectivity 2- hydroxy-5, 6-dihydro-Wl, eoxazinea 3, cis-octahydro [l, 4] oxazino [3, 2-b] oxazines 4, a- imino ketones 6, 2-acetyl-1, 3-oxazolidines 7, NJV'-bis (2-hydroxy-2-methylpropyl)-2, 3- butanediimines 8, and 2, 2'-dimethyl-2, 2'-bioxazolidines 9 depending on the nature of the ...