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Issue 45, 2017
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α-Trifluoromethylated tertiary homoallylic amines: diastereoselective synthesis and conversion into β-aminoesters, γ- and δ-aminoalcohols, azetidines and pyrrolidines

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Abstract

The diastereoselective addition of allyl zinc and allylindium derivatives to α-trifluoromethyl N-tert-butanesulfinyl hemiaminals, bench stable precursors of aryl and alkyl trifluoromethyl ketimines, allows the synthesis of homoallylic amines containing a tetrasubstituted carbon stereocentre bearing a trifluoromethyl group with good diastereoselectivities (up to dr > 99 : 1). This approach was also suitable for accessing chiral homoallylic amines bearing two contiguous stereocenters. The synthetic usefulness of N-tert-butanesulfinyl homoallylamines was illustrated by preparing various trifluoromethylated nitrogen containing bifunctional synthons (aminoesters, aminoalcohols) and small azaheterocycles (azetidines, pyrrolidines).

Graphical abstract: α-Trifluoromethylated tertiary homoallylic amines: diastereoselective synthesis and conversion into β-aminoesters, γ- and δ-aminoalcohols, azetidines and pyrrolidines

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Publication details

The article was received on 10 Oct 2017, accepted on 01 Nov 2017 and first published on 10 Nov 2017


Article type: Paper
DOI: 10.1039/C7OB02506H
Citation: Org. Biomol. Chem., 2017,15, 9696-9709
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    α-Trifluoromethylated tertiary homoallylic amines: diastereoselective synthesis and conversion into β-aminoesters, γ- and δ-aminoalcohols, azetidines and pyrrolidines

    F. Grellepois, A. Ben Jamaa and N. Saraiva Rosa, Org. Biomol. Chem., 2017, 15, 9696
    DOI: 10.1039/C7OB02506H

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