Stereoselective Synthesis of the Four Stereoisomers of 4-(N,N-Dibenzylamino)-2,2-dimethyl-3-hydroxypentanenitrile |
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Authors: | Robert M Moriarty Anping Tao Sudersan M Tuladhar |
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Institution: | 1. Department of Chemistry , University of Illinois at Chicago , Chicago, IL, 60607;2. Steroids, Ltd , 2201 West Campbell Park Drive, Chicago, IL, 60612, USA;3. Steroids, Ltd , 2201 West Campbell Park Drive, Chicago, IL, 60612, USA |
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Abstract: | The title compounds 1(a,b) and 1(c,d) were synthesized by (i) non-chelation controlled sodium borohydride reduction of their corresponding α-N,N-dibenzylaminoketones and (ii) the Aldol-type condensation of optically pure N,N-dibenzylaminoaldehydes with the lithium derivative of isobutyronitrile, respectively. Attempted inversion of configurations of these secondary alcohols using the Moriarty method yielded 4-chloro-3-N,N-dibenzylaminonitrile via an aziridinium ion intermediate instead of the expected inverted alcohols. |
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