ol9b00622_si_001.pdf (4.26 MB)
Access to Unprotected β‑Fluoroalkyl β‑Amino Acids and Their α‑Hydroxy Derivatives
journal contribution
posted on 2019-03-15, 11:19 authored by Volodymyr Sukach, Serhii Melnykov, Sylvain Bertho, Iryna Diachenko, Pascal Retailleau, Mykhailo Vovk, Isabelle GillaizeauUnprotected
β-(het)aryl-β-fluoroalkyl β-amino
acids and their α-hydroxy derivatives can be readily obtained
using a decarboxylative Mannich-type reaction without protection/deprotection
steps. This protocol utilizes lithium hexamethyldisilazide and (het)arylfluoroalkyl
ketones to generate NH-ketimine intermediates. The mild reaction conditions
allow the preparation of original fluorinated β-amino acids
as useful building blocks in a practical and scalable manner.