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Synthesis 1992; 1992(1/2): 229-234
DOI: 10.1055/s-1992-34183
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A Diastereoselective Synthesis of (dl)-1,3-Diphenyl-1,3-propanediamines

Scott E. Denmark* , Jung-Ho Kim
  • *Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA
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Publication Date:
18 September 2002 (online)

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A large-scale and practical synthesis of (dl)-1,3-diphenyl-1,3-propanediamine (1) has been achieved by a highly diastereoselective phenylcerium dichloride addition to 1-tert-butoxycarbonyl-4,5-dihydro-5-phenylpyrazole (3). Alkylcerium addition reaction to the corresponding 5-alkyl substituted 1-Boc-4,5-dihydropyrazoles was less satisfactory mainly giving ring-cleaved products. Further elaboration of the diamine 1 to the N-substituted derivatives 8a-f bearing N-methyl, N-ethyl, N-isopropyl, N-neopentyl, N-benzyl, and N-mesitylmethyl groups is described.