Access to Unprotected β‑Fluoroalkyl β‑Amino Acids and Their α‑Hydroxy Derivatives
Posted on 2019-03-15 - 11:19
Unprotected
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.
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Sukach, Volodymyr; Melnykov, Serhii; Bertho, Sylvain; Diachenko, Iryna; Retailleau, Pascal; Vovk, Mykhailo; et al. (2019). Access to Unprotected β‑Fluoroalkyl β‑Amino Acids and Their α‑Hydroxy Derivatives. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b00622
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AUTHORS (7)
VS
Volodymyr Sukach
SM
Serhii Melnykov
SB
Sylvain Bertho
ID
Iryna Diachenko
PR
Pascal Retailleau
MV
Mykhailo Vovk
IG
Isabelle Gillaizeau