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ChemInform Abstract: Diastereoselective Addition of Metal-Coordinated and “Naked” Nucleophilic Reagents to Norephedrine Derived 2-Acyl-N-tosyl- oxazolidines.

✍ Scribed by G. POLI; E. MACCAGNI; L. MANZONI; T. PILATI; C. SCOLASTICO

Publisher: John Wiley and Sons
Year: 2010
Weight: 30 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199720121

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✦ Synopsis

Diastereoselective Addition of Metal-Coordinated and "Naked" Nucleophilic Reagents to Norephedrine Derived 2-Acyl-N-tosyl-oxazolidines.

-Under chelating or non-coordinating conditions the addition of tris-s-butyl borohydrides to (I) can be directed with high selectivity. Under these conditions the reduction of the phenyl ketone (IV) is totally selective. Grignard reagents and organolithiums also add to the ketones with remarkable selectivity.

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