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ChemInform Abstract: 1,3-Diphenylpropane-1,3-diamines. Part 11. Conversion of a 3-Hydroxy-1,3-diphenylpropan-1-one to 1,3-Diphenylpropane-1,3-diamines.

✍ Scribed by A. KAISER; P. BIELMEIER; W. WIEGREBE

Publisher: John Wiley and Sons
Year: 2010
Weight: 37 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199812085

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✦ Synopsis

12 -085

1,3-Diphenylpropane-1,3-diamines.

Part 11. Conversion of a 3-Hydroxy-1,3-diphenylpropan-1-one to 1,3-Diphenylpropane-1,3diamines. -Highly diastereoselective BH 3 •THF syn-reduction of the BBr 3 complex of hydroxypropanone (I) affords meso-diol (II), whereas a mixture of meso-diol (II) and racemate (IV) is obtained by BH 3 •THF reduction without complexation. The corresponding diamines (III) and (V) are easily accessible in three more reaction steps, involving a clean inversion during substitution.

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