α-Trifluoromethylated tertiary homoallylic amines: diastereoselective synthesis and conversion into β-aminoesters, γ- and δ-aminoalcohols, azetidines and pyrrolidines - Université de Reims Champagne-Ardenne Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2017

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).
Fichier principal
Vignette du fichier
hal obc 2017.pdf (1.09 Mo) Télécharger le fichier
Origin Files produced by the author(s)

Dates and versions

hal-01886710 , version 1 (15-02-2022)

Licence

Identifiers

Cite

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 & Biomolecular Chemistry, 2017, 15 (45), pp.9696 - 9709. ⟨10.1039/c7ob02506h⟩. ⟨hal-01886710⟩
20 View
61 Download

Altmetric

Share

Gmail Mastodon Facebook X LinkedIn More