Asymmetric Synthesis of Both Enantiomers of α-Trifluoromethyl Substituted Homoallylamine

Kazumasa  Funabiki; Masashi  Nagamori; Masaki  Matsui; Dieter  Enders

doi:10.1055/s-2002-35631

SPECIALTOPIC

Asymmetric Synthesis of Both Enantiomers of α-Trifluoromethyl Substituted Homoallylamine

Kazumasa Funabiki*^a, Masashi Nagamori^a, Masaki Matsui^a, Dieter Enders^b
^a Department of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
Fax: +81(58)2301893; e-Mail: kfunabik@apchem.gifu-u.ac.jp;
^b Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany

Abstract

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Abstract

An efficient asymmetric synthesis of both enantiomers of α-trifluoromethylated homoallylamine via nucleophilic allylation of trifluoroacetaldehyde SAMP- or RAMP-hydrazone, followed by benzoylation and SmI₂-promoted nitrogen-nitrogen single bond cleavage is described.

Key words

asymmetric synthesis - fluorine - hydrazone - allylation - amines

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References

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9

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