Stereoselective synthesis of the four stereoisomers of 4-(N,N- dibenzylamino)-2,2-dimethyl-3-hydroxypentanenitrile

Article abstract of DOI:10.1080/00397919708004183

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.

Full text of DOI:10.1080/00397919708004183

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Synthetic Communications: An
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Stereoselective Synthesis of
the Four Stereoisomers of
4-(N,N-Dibenzylamino)-2,2-
dimethyl-3-
hydroxypentanenitrile
Robert M. Moriarty a b , Anping Tao a & Sudersan M.
Tuladhar b
a Department of Chemistry , University of Illinois at
Chicago , Chicago, IL, 60607
b Steroids, Ltd , 2201 West Campbell Park Drive,
Chicago, IL, 60612, USA
Published online: 22 Aug 2006.
To cite this article: Robert M. Moriarty , Anping Tao & Sudersan M. Tuladhar (1997)
Stereoselective Synthesis of the Four Stereoisomers of 4-(N,N-Dibenzylamino)-2,2-
dimethyl-3-hydroxypentanenitrile, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 27:18, 3227-3234,
DOI: 10.1080/00397919708004183
To link to this article: http://dx.doi.org/10.1080/00397919708004183
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