Synthesis of a novel N-hydroxypyrrolidine using enzyme catalysed asymmetric carbon–carbon bond synthesis

N-Hydroxypyrrolidine 5 has been prepared in nine steps starting from 3-O-benzylglyceraldehyde 13. The synthetic route employs Escherichia coli transketolase mediated C–C bond synthesis to establish the absolute stereochemistry and a subsequent ring contraction of a 1,2-oxazine 17 to provide the N-hydroxypyrrolidine nucleus.