Highly functionalized cyclic and bicyclic beta-amino acids from suga beta-nitroesters

摘要

The synthesis of highly functionalized bicyclic and cyclic beta-amino acids from beta-nitrosugars is reported. Specifically, our strategy for the synthesis of polyhydroxylated cyclopentane beta-amino acids via the intramolecular C-alkylation of 6-nitro-2-O-triflates of furanosides has been applied to the preparation of the first two examples of a novel class of bicyclic beta-amino acids and a novel cyclopentene beta-amino acid. Also, our Henry reaction mediated strategy for the synthesis of polyhydroxylated cyclohexane beta-amino acids has been extended to a divergent, stereoselective synthesis of new polysubstituted cyclohexane and cyclopentane beta-amino acids. (C) 2019 Published by Elsevier Ltd.