Metal-free hydroxy and aminocyanation of furanos-3-uloses

TSAO-T and ATSAO-T analogues are molecules of interest that are able to inhibit the reverse transcriptase (RT) of HIV-1 and HCV. We also recently highlighted their antiproliferative properties. In all cases, the spiro cycle was a required group for biological activities, which led chemists to produce many derivatives, especially on this ring. These structures can be accessed through the formation of glycoaminonitriles and glycocyanhydrins using methodologies not always adapted to the synthesis of large quantities. Moreover, these latter are poorly versatile (substrate-dependent), need expensive cyanogenic agents and implies the use of a metal in non-catalytic amounts. For this reason, we report here a new metal-free methodology for the synthesis of glycoaminonitriles and glycocyanhydrins using molecular iodine (I2). [Display omitted] •The synthesis of glycoaminonitriles and glycocyanhydrins was carried out using molecular iodine (I2).•It is a versatile and metal free Strecker reaction.•The preparation of aminonitriles and cyanohydrins is stereoselective.•Reaction times did not influence the stereoselectivity, the reaction leading to products having an allo or ribo configuration.