Orthogonally protected glycerols and 2-aminodiols, useful building blocks in heterocyclic chemistry

Abstract

The efficient synthesis of orthogonally protected glycerols, 2-aminopropane-1,3-diols and 2-aminobutane-1,4-diols that can constitute useful tools in heterocyclic chemistry, is reported. These interesting tri-functionalized small synthons were easily prepared from serine or aspartic acid. In addition, these substrates can be readily transformed into their iodide derivatives in very good yields.

Synthesis of 1,4-Oxazepane-2,5-diones via Cyclization of Rotationally Restricted Amino Acid Precursors and Structural Reassignment of Serratin

“…Reductive amination of glycine methyl ester hydrochloride 10d with anisaldehyde 13b gave N-PMB-protected methyl glycinate 14b in a good yield (Scheme ). The same N-acylation and cyclization conditions used for the synthesis of the N -benzyl derivative 17a were applied to yield the N-PMB-protected seven-membered ring-containing compound 17b (Scheme ).…”