作者:Eva Van Hende、Guido Verniest、Frederik Deroose、Jan-Willem Thuring、Gregor Macdonald、Norbert De Kimpe
DOI:10.1021/jo802791r
日期:2009.3.6
Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated beta-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromofluorination of N-(diphenylmethylidcne)-2-(4-methoxyphenoxymethyl)-2-propenylamine, yielding 1-diphenylmethyl-3-hydroxymethyl-3-fluoroazetidine after reduction of the imino bond, ring closure, and removal of the 4-methoxybenzyl group. Changing the N-protecting group to a Boc-group allows further oxidation to 1-Boc-3-fluoroazetidine3-carboxylic acid, a new fluorinated heterocyclic amino acid.