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

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Publication
https://doi.org/10.1021/acs.orglett.9b00622
Domain
Life & Health Sciences
Fellow
Volodymyr Sukach

Org. Lett. 2019, 21, 7, 2340–2345

Volodymyr Sukach1,2, Serhii Melnykov3,4, Sylvain Bertho2, Iryna Diachenko2, Pascal Retailleau5, Mykhailo Vovk3, and Isabelle Gillaizeau2

 

1 Le Studium Loire Valley Institute for Advanced Studies, 1, rue Dupanloup, Orléans 45000, France

2 Institute of Organic and Analytical Chemistry, ICOA UMR 7311 CNRS, Universitéd’Orléans, rue de Chartres, Orléans 45100,France

3 Institute of Organic Chemistry of NAS of Ukraine, 5, Murmanska Str., Kyiv 02660, Ukraine

4 Enamine LTD, 78 Chervonotkats’ka Str., Kyiv 02094, Ukraine

5 Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Avenue de laTerrasse, Gif-sur-Yvette 91198, France

Abstract

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.

Keywords

β‑Fluoroalkyl
β-Amino Acids
α-Hydroxy Derivatives
Proteins
Peptides
lithium hexamethyldisilazide
NH-ketimine intermediates
Published by

American Chemical Society