A diastereoselective synthesis of (dl)-1,3-diphenyl-1,3-propanediamines

S. E. Denmark, J. H. Kim

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)229-234
Number of pages6
JournalSynthesis
Issue number1-2
DOIs
StatePublished - Jan 1 1992

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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