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Versatile Stereocontrol in Kinetic Resolution of a Diphenylphosphinyl-Protected α-Amino Aldehyde by Reaction with Chiral Phosphonates

Kreuder, Reinhard ; Rein, Tobias ; Reiser, Oliver



Abstract

In kinetic resolutions of the racemic aldehyde 1 by reaction with chiral phosphonates of type 2, all of which contain the same chiral auxiliary in the same enantiomeric form, any of the four diastereomers 3a, 3b, 4a or 4b can be obtained as the main product by an appropriate choice of reaction parameters (geometric selectivities from 66:34 to 98:2, diastereomer ratios between 93:7 and ≥99:1). The ...

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