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Issue 34, 2012
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Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids

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Abstract

Organic base-catalyzed reaction of (S)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine with dialkyl malonates was found to be effective for synthesis of both (S,SS) and (R,SS) β-aminomalonates in high yield with good to excellent diastereoselectivity (76–98% de). The products of this Mannich reaction provide direct access to β-trifluoromethyl-β-alanine of either (R) or (S) absolute configuration.

Graphical abstract: Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids

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Article information


Submitted
28 Jan 2012
Accepted
05 Mar 2012
First published
06 Mar 2012

Chem. Commun., 2012,48, 4124-4126
Article type
Communication

Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids

N. Shibata, T. Nishimine, N. Shibata, E. Tokunaga, K. Kawada, T. Kagawa, A. E. Sorochinsky and V. A. Soloshonok, Chem. Commun., 2012, 48, 4124
DOI: 10.1039/C2CC30627A

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