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

V. A. Sukach | Zendy; Serhii Melnykov | Zendy; Sylvain Bertho | Zendy; Iryna Diachenko | Zendy; Pascal Retailleau | Zendy; М. В. Вовк | Zendy; Isabelle Gillaizeau | Zendy

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

Author(s) -

V. A. Sukach,

Serhii Melnykov,

Sylvain Bertho,

Iryna Diachenko,

Pascal Retailleau,

М. В. Вовк,

Isabelle Gillaizeau

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b00622

Subject(s) - chemistry , amino acid , aryl , lithium (medication) , combinatorial chemistry , reaction conditions , organic chemistry , catalysis , biochemistry , medicine , alkyl , endocrinology

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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