TY - JOUR
T1 - A diastereoselective synthesis of (dl)-1,3-diphenyl-1,3-propanediamines
AU - Denmark, S. E.
AU - Kim, J. H.
PY - 1992
Y1 - 1992
N2 - 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.
AB - 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.
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U2 - 10.1055/s-1992-34183
DO - 10.1055/s-1992-34183
M3 - Article
AN - SCOPUS:0026532202
SN - 0039-7881
SP - 229
EP - 234
JO - Synthesis
JF - Synthesis
IS - 1-2
ER -