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

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017, Vol.15 (45), p.9696-979
Main Authors: Grellepois, Fabienne, Ben Jamaa, Abdelkhalek, Saraiva Rosa, Nathalie
Format: Article
Language:English
Subjects:
Amines
Aromatic compounds
Chemical Sciences
Imines
Nitrogen
Organic chemistry
Synthesis
Zinc
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Summary: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). The diastereoselective synthesis and the functionalization of homoallylic tertiary carbinamines containing a tetrasubstituted carbon stereocentre bearing a trifluoromethyl group are described.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02506h