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Synthesis of Enantiopure o-Hydroxybenzylamines by Stereoselective Reduction of 2-Imidoylphenols: Application in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes (1999)

Palmieri, Gianni

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 805-811

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ISSN: 1434-193X

Keywords: Aminophenols /Asymmetric synthesis ; C-C coupling ; Reductions ; Conformation analysis ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: -Enantiopure o-hydroxybenzylamines 2a-i were synthesized by diastereoselective reduction of the 2-imidoylphenols (R)-1a-i. Conformational analysis enabled the assignment of the absolute configurations of compounds 2a-i. The accessible o-hydroxybenzylamine (R,R)-2h serves as an effective catalyst precursor for highly enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes. This pathway represents a practical and operationally very simple methodology for the enantioselective synthesis of both the enantiomers of secondary alcohols 7a-f.

Additional Material: 4 Ill.

Type of Medium: Electronic Resource

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