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

✍ Scribed by Andrew J Humphrey; Simon F Parsons; Mark E.B Smith; Nicholas J Turner

• Book ID: 104210383
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 136 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00645-6

✦ Synopsis

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.