Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/75832
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Type: Journal article
Title: A study on the diastereoselective synthesis of α-fluorinated β³-amino acids by α-fluorination
Other Titles: A study on the diastereoselective synthesis of alpha-fluorinated beta(3)-amino acids by alpha-fluorination
Author: Peddie, V.
Abell, A.
Citation: Helvetica Chimica Acta, 2012; 95(12):2460-2473
Publisher: Wiley-V C H Verlag GMBH
Issue Date: 2012
ISSN: 0018-019X
1522-2675
Statement of
Responsibility: 
Victoria Peddie and Andrew D. Abell
Abstract: The treatment of a β3-amino acid methyl ester with 2.2 equiv. of lithium diisopropylamide (LDA), followed by reaction with 5 equiv. of N-fluorobenzenesulfonimide (NFSI) at -78° for 2.5h and then 2h at 0°, gives syn-fluorination with high diastereoisomeric excess (de). The de and yield in these reactions are somewhat influenced by both the size of the amino acid side chain and the nature of the amine protecting group. In particular, fluorination of N-Boc-protected β3-homophenylalanine, β3-homoleucine, β3-homovaline, and β3-homoalanine methyl esters, 5 and 9-11, respectively, all proceeded with high de (>86% of the syn-isomer). However, fluorination of N-Boc-protected β3-homophenylglycine methyl ester (16) occurred with a significantly reduced de. The use of a Cbz or Bz amine-protecting group (see 3 and 15) did not improve the de of fluorination. However, an N-Ac protecting group (see 17) gave a reduced de of 26%. Thus, a large N-protecting group should be employed in order to maximize selectivity for the syn-isomer in these fluorination reactions. Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.
Keywords: Amino acids
Fluorine compounds
Stereoselective synthesis
Rights: © 2012 Verlag Helvetica Chimica Acta AG, Zurich
DOI: 10.1002/hlca.201200520
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