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

Org. Lett. 2019, 21 (7), 2340-2345

DOI: 10.1021/acs.orglett.9b00622

Sukach V.; Melnykov S.; Bertho S.; Diachenko I.; Retailleau P.; Vovk M.; Gillaizeau I.

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.

Access to Unprotected beta-Fluoroalkyl beta-Amino Acids and Their alpha-Hydroxy Derivatives


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