Synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl) serine as potential in vivo precursors of fluorinated norepinephrines

Authors
Herbert, B Kim, IH Kirk, KL
Citation
B. Herbert et al., Synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl) serine as potential in vivo precursors of fluorinated norepinephrines, J ORG CHEM, 66(14), 2001, pp. 4892-4897
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
14
Year of publication
2001
Pages
4892 - 4897
Database
ISI
SICI code
0022-3263(20010713)66:14<4892:SO2A6S>2.0.ZU;2-C
Abstract
The title compounds were prepared by the aldol condensation of 3,4-dibenzyl oxy-2-fluorobenzaldehyde and 4,5-dibenzyloxy-2-fluorobenzaldehyde with the oxazolidinone 2, a chiral glycine equivalent. Removal of the chiral auxilia ry and blocking groups produced the target amino acids 2-fluoro- and 6-fluo ro-(2S,3R)-(3,4-dihydroxyphenyl)serine (1b and 1c) in > 98% ee.