Issue 27, 2016

A diastereoselective Mannich-type reaction of α-fluorinated carboxylate esters: synthesis of β-amino acids containing α-quaternary fluorinated carbon centers

Abstract

We report a diastereoselective Mannich-type reaction of α-alkyl, α-aryl, and α-vinyl fluoroacetates with N-tert-butylsulfinyl imines. This method provides a powerful means to access a broad range of highly functionalized β-amino acids containing α-fluorinated quaternary stereogenic carbon centers. We also show that the stereochemical outcome of the present reaction is highly dependent on the steric and electronic properties of the fluorocarbon nucleophiles. This protocol uses readily available starting materials, tolerates a variety of functional groups, and is operationally simple.

Graphical abstract: A diastereoselective Mannich-type reaction of α-fluorinated carboxylate esters: synthesis of β-amino acids containing α-quaternary fluorinated carbon centers

Supplementary files

Article information

Article type
Paper
Submitted
18 May 2016
Accepted
31 May 2016
First published
01 Jun 2016

Org. Biomol. Chem., 2016,14, 6457-6462

A diastereoselective Mannich-type reaction of α-fluorinated carboxylate esters: synthesis of β-amino acids containing α-quaternary fluorinated carbon centers

X. Li, Y. Li and H. Shang, Org. Biomol. Chem., 2016, 14, 6457 DOI: 10.1039/C6OB01084A

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