Reactivity of gamma-hydroxy-alpha,beta-acetylenic esters with amines: facile synthesis of the optically active 4-amino-2(5H)-furanones.
A convenient synthesis of the optically active 4-amino-2(5H)-furanones is discovered by combining an asymmetric alkyne addition to aldehydes and a subsequent aliphatic amine addition. Both steps can be conducted at room temperature and the products are obtained with high enantioselectivity (84-90% ee). The 4-amino-2(5H)-furanones are also found to undergo very facile electrophilic substitution reactions.
Zhou
Li-Hong
LH
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA.
Yu
Xiao-Qi
XQ
Pu
Lin
L
D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D004952:Esters; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000447:Aldehydes; D000480:Alkynes; D000588:Amines; D004952:Esters; D005663:Furans