One-pot stereoselective synthesis of 1,2-amino alcohol derivatives

Common β-hydroxy amino acids (such as threonine) can be readily transformed into 1,2-amino alcohols with excellent stereoselectivity. This one-pot decarboxylation-alkylation process allows the replacement of the carboxyl group by alkyl, allyl, or aryl groups, generally in high yields. A variation of the process (decarboxylation-Diels-Alder) allows the formation of bi- and polycyclic systems, which are useful precursors of alkaloid cores or iminosugars.
This work was supported by the Research Program CTQ2009-07109 of the Plan Nacional de Investigación Científica, Desarrollo e Innovación Tecnológica, Ministerio de Ciencia e Innovación, Spain. We also acknowledge financial support from FEDER funds. I.R.E. thanks CSIC for a predoctoral JAE fellowship.