The synthesis of trifluoromethylated γ-amino alcohols through an eco-friendly one-pot self-catalysed Mannich-type reaction between N-protected trifluoromethyl aldimines and suitable cyclic or acyclic α,α-dialkyl aldehydes has been developed. Good yields, mild reaction conditions and simple experimental work-up procedures are some of the advantages of this method. Starting from optically pure trifluoromethyl aldimines, target compounds, also having a quaternary stereocentre, can be obtained in good to excellent diastereoselectivities.

β,β-Dialkyl γ-amino γ-trifluoromethyl alcohols from trifluoromethyl (E)-aldimines by a one-pot solvent-free Mannich-type reaction and subsequent reduction / Fioravanti, Stefania; Mancinelli, Federico; Parise, Luca; Pelagalli, Alessia; Pellacani, Lucio; Trulli, Laura. - In: RSC ADVANCES. - ISSN 2046-2069. - STAMPA. - 6:(2016), pp. 101862-101868. [10.1039/C6RA22507A]

β,β-Dialkyl γ-amino γ-trifluoromethyl alcohols from trifluoromethyl (E)-aldimines by a one-pot solvent-free Mannich-type reaction and subsequent reduction

FIORAVANTI, Stefania
Primo
;
MANCINELLI, FEDERICO
Secondo
;
PELAGALLI, ALESSIA;PELLACANI, Lucio
Penultimo
;
TRULLI, LAURA
Ultimo
2016

Abstract

The synthesis of trifluoromethylated γ-amino alcohols through an eco-friendly one-pot self-catalysed Mannich-type reaction between N-protected trifluoromethyl aldimines and suitable cyclic or acyclic α,α-dialkyl aldehydes has been developed. Good yields, mild reaction conditions and simple experimental work-up procedures are some of the advantages of this method. Starting from optically pure trifluoromethyl aldimines, target compounds, also having a quaternary stereocentre, can be obtained in good to excellent diastereoselectivities.
2016
solvent-free reactions; Mannich-type reactions; fluorinated compounds
01 Pubblicazione su rivista::01a Articolo in rivista
β,β-Dialkyl γ-amino γ-trifluoromethyl alcohols from trifluoromethyl (E)-aldimines by a one-pot solvent-free Mannich-type reaction and subsequent reduction / Fioravanti, Stefania; Mancinelli, Federico; Parise, Luca; Pelagalli, Alessia; Pellacani, Lucio; Trulli, Laura. - In: RSC ADVANCES. - ISSN 2046-2069. - STAMPA. - 6:(2016), pp. 101862-101868. [10.1039/C6RA22507A]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/894228
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