1,3-Diphenylpropane-1,3-diamines - XI. Conversion of a 3-hydroxy-1,3-diphenylpropan-1-one to 1,3-diphenylpropane-1,3-diamines

Kaiser, A. and Bielmeier, P. and Wiegrebe, Wolfgang (1997) 1,3-Diphenylpropane-1,3-diamines - XI. Conversion of a 3-hydroxy-1,3-diphenylpropan-1-one to 1,3-diphenylpropane-1,3-diamines. MONATSHEFTE FUR CHEMIE, 128 (12). pp. 1247-1254. ISSN 0026-9247, 1434-4475

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Abstract

Highly diastereoselective BH3/THF syn-reduction of the 3-hydroxy-1,3 -diphenylpropan-1-one/BBr3 complex 3/BBr3 (cf. Sarko) afforded the meso-diol 4, whereas racemate 5 was obtained by BH3/THF reduction without complexation. Mesylation, exchange of mesylate by azide, and reduction with SnCl2/thiophenol led to the diamines 10 and 11 which were also produced by reductive N-N cleavage of the 4,5-dihydropyrazole 13.

Item Type: Article
Uncontrolled Keywords: PT(II) COMPLEXES; KETONES; ESTERS; 1,3-diphenylpropane-1,3-diamines; 3-hydroxy-1,3-diphenylpropan-1-one; 3,5-diphenyl-4,5-dihydropyrazole; syn-reduction of beta-hydroxyketones
Subjects: 600 Technology > 615 Pharmacy
Divisions: Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Wiegrebe
Depositing User: Dr. Gernot Deinzer
Date Deposited: 02 Mar 2023 06:31
Last Modified: 02 Mar 2023 06:31
URI: https://pred.uni-regensburg.de/id/eprint/50377

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