Access to Unprotected β‑Fluoroalkyl β‑Amino Acids and Their α‑Hydroxy Derivatives

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-ketim...

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Bibliographic Details
Published in:Organic letters 2019-04, Vol.21 (7), p.2340-2345
Main Authors: Sukach, Volodymyr, Melnykov, Serhii, Bertho, Sylvain, Diachenko, Iryna, Retailleau, Pascal, Vovk, Mykhailo, Gillaizeau, Isabelle
Format: Article
Language:English
Subjects:
Chemical Sciences
Life Sciences
Organic chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00622