Three-component assembly of amines, boronic acids, and a polyfunctionalized furanose: a concise entry to furanose-based carbohydrate templates.
A highly functionalyzed furanose derivative, accessible in five steps from D-mannose, comprising a halo-alkenyl allylic-oxirane system, undergoes a palladium catalyzed one-pot, three component, assembly with boronic acids (or alkyl boranes) and amines to give, in a complete regio- and stereocontrolled manner, a sugar based derivative with two sites of molecular diversity.
Gómez
Ana M
AM
Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain. anagomez@iqog.csic.es
Barrio
Aitor
A
Pedregosa
Ana
A
Valverde
Serafín
S
López
J Cristóbal
JC