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Lewis acid activation of chiral 2-trifluoromethyl-1,3-oxazolidines. Application to the stereoselective synthesis of trifluoromethylated amines, α- and β-amino acids

✍ Scribed by Nicolas Lebouvier; Christophe Laroche; Florent Huguenot; Thierry Brigaud

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 84 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00330-1

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✦ Synopsis

The reaction of chiral 2-trifluoromethyl-1,3-oxazolidines with various silylated nucleophiles under Lewis acid activation provides a stereoselective route to functionalized a-trifluoromethylamines. This methodology was successfully applied to the diastereoselective synthesis of trifluoromethylated homoallylic and propargylic amines, trifluoromethylated a-amino nitrile, b-aminoketone and b-aminoester. The a-amino nitrile and the b-amino ester were converted into (+)-3,3,3-trifluoroalanine and (+)-4,4,4-trifluoro-3-aminobutanoic acid in a one-step procedure.

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