Stereoselective Synthesis of Orthogonally Protected 1,2-Diaminoinositols from D-Mannose

作者：Acurcio Rita C; Soengas Raquel G^*; Almeida Paz Filipe A; Silva Artur M S

来源：Synlett, 2014, 25(15): 2217-2220.

DOI：10.1055/s-0034-1378545

• Henry reaction
• aza-Henry reaction
• bromonitro-alkanes
• 1,2-diaminoinositols
• 2-nitroamines

We present herein a promising novel strategy for the transformation of sugar aldehydes into 1,2-diaminoinositols. This process, based on the sequential intermolecular aza-Henry reaction and intermolecular Henry reaction allowed the total synthesis of a 1,2-diaminoinositols with total stereochemical control. The new route constitutes a simpler and more efficient approach than those previously described routes to 1,2-diaminoinositols and it has the additional advantage of offering the possibility of orthogonal protection of the amino groups.

• 出版日期2014-9