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2005
Amines
Q 0120
12- 079
Organocatalyzed Solvent-Free Aza-Henry Reaction: A Breakthrough in the
One-Pot Synthesis of 1,2-Diamines. — Tetramethylguanidine is found to be an effective catalyst for the synthesis of nitroamines (III) from imines (I) and nitroalkanes (II)
in excellent yields and high diastereomeric ratios. The reduction of the nitro group in
compounds (III) is successfully performed by use of stoichiometric amounts of zinc
combined with catalytic amounts of indium in the presence of saturated NH4Cl as a proton source. The resulting diamines are finally converted into more stabile disulfonamides (VIII) and (X). — (BERNARDI*, L.; BONINI, B. F.; CAPITO, E.; DESSOLE,
G.; COMES-FRANCHINI, M.; FOCHI, M.; RICCI*, A.; J. Org. Chem. 69 (2004) 23,
8168-8171; Dip. Chim. Org. "A. Mangini", Univ. Bologna, I-40136 Bologna, Italy;
Eng.) — Klein
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