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

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).
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https://hal.univ-reims.fr/hal-01886710
Contributor : Fabienne Grellepois <>
Submitted on : Wednesday, October 3, 2018 - 10:37:23 AM
Last modification on : Tuesday, December 17, 2019 - 2:26:00 AM

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Fabienne Grellepois, Abdelkhalek Ben Jamaa, Nathalie Saraiva Rosa. α-Trifluoromethylated tertiary homoallylic amines: diastereoselective synthesis and conversion into β-aminoesters, γ- and δ-aminoalcohols, azetidines and pyrrolidines. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2017, 15 (45), pp.9696 - 9709. ⟨10.1039/c7ob02506h⟩. ⟨hal-01886710⟩

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