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

Authors
Humphrey, AJ Parsons, SF Smith, MEB Turner, NJ
Citation
Aj. Humphrey et al., Synthesis of a novel N-hydroxypyrrolidine using enzyme catalysed asymmetric carbon-carbon bond synthesis, TETRAHEDR L, 41(22), 2000, pp. 4481-4485
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
22
Year of publication
2000
Pages
4481 - 4485
Database
ISI
SICI code
0040-4039(20000608)41:22<4481:SOANNU>2.0.ZU;2-1
Abstract
N-Hydroxypyrrolidine 5 has been prepared in nine steps starting from;3-O-be nzylglyceraldehyde 13. The synthetic route employs Escherichia coli transke tolase mediated C-C bond synthesis to establish the absolute stereochemistr y and a subsequent ring contraction of a 1,2-oxazine 17 to provide the N-hy droxypyrrolidine nucleus. (C) 2000 Elsevier Science Ltd. All rights reserve d.