The products of the condensation reactions of twenty-six different 1,2-amino alcohols with excess aqueous formaldehyde were identified, with the help of a simple and effective analytical technique based on mass spectroscopy. With a few exceptions, which arise from steric or solubility effects, most amino alcohols form bis(oxazolidine)methane adducts preferentially.
Treatment of chiral amino alcohols 1 with an excess of formaldehyde followed by reaction with NaOH at room temperature provides optically active C-2-symmetric N,N'-methylenebisoxazolidines 2 in high yield.
Salas-Coronado, Raul; Galvez-Ruiz, Juan Carlos; Guadarrama-Perez, Carlos, Heterocycles, 2003, vol. 60, # 5, p. 1123 - 1132
作者:Salas-Coronado, Raul、Galvez-Ruiz, Juan Carlos、Guadarrama-Perez, Carlos、Flores-Parra, Angelina