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Issue 36, 2017
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Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids

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Abstract

We report a one-pot synthesis of chiral β2,2,3-amino acids by the Mannich addition of bistrimethylsilyl ketene acetals to N-tert-butanesulfinyl imines followed by the removal of the chiral auxiliary. The synthesis and isolation of pure β-amino acid hydrochlorides were conducted under mild conditions, without strong bases and this method is operationally simple. The stereoselective reaction was promoted by two different activation methods that lead to different stereoisomers: (1) Lewis Acid (LA) catalysis with boron trifluoride diethyl etherate and (2) Lewis Base (LB) catalysis with tetrabutylammonium difluorotriphenylsilicate. The reaction presented good diastereoselectivity with LB activation and moderate to good dr with LA catalysis. The exceptions in both protocols were imines with electron donating groups in the aromatic ring.

Graphical abstract: Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids

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Publication details

The article was received on 26 Jul 2017, accepted on 23 Aug 2017 and first published on 24 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01853C
Citation: Org. Biomol. Chem., 2017,15, 7705-7709
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    Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids

    M. Cantú-Reyes, I. Alvarado-Beltrán, R. Ballinas-Indilí, C. Álvarez-Toledano and M. Hernández-Rodríguez, Org. Biomol. Chem., 2017, 15, 7705
    DOI: 10.1039/C7OB01853C

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