Organocatalyzed Solvent-Free Aza-Henry Reaction: A Breakthrough in the One-Pot Synthesis of 1,2-Diamines
The Journal of Organic Chemistry2004Vol. 69(23), pp. 8168–8171
Citations Over TimeTop 12% of 2004 papers
Luca Bernardi, Bianca F. Bonini, Elena Capitò, Gabriella Dessole, Mauro Comes Franchini, Mariafrancesca Fochi, Alfredo Ricci
Abstract
A nitrogen-containing superbase such as TMG was found to be an effective catalyst for the reaction between N-diphenylphosphinoyl imines and nitroalkanes. Exploiting a protocol that avoids the use of any solvent also during workup procedure, we synthesized a series of beta-nitroamines in excellent yields and high diastereomeric ratios. These results, combined with the capability of the indium in conjunction with Zn as the stoichiometric reducing agent to perform in aqueous medium reduction of the nitro group under mild reaction conditions, led us to devise a three-step, one-pot synthesis of a range of 1,2-diamines, making use of environmentally friendly procedures in the various steps.
Related Papers
- → Synthesis of guanidinophosphazene superbase for the facile preparation of high molecular weight polysiloxane under mild conditions(2022)8 cited
- → Diastereomer-Differentiating Photochemistry of β-Arylbutyrophenones: Yang Cyclization versus Type II Elimination(2005)25 cited
- → Compound Separation by Cyclic, Selective Dissolution. Isolation of Diastereomeric, 1β-Methylcarbapenem Key Intermediates(1993)3 cited
- → Synthesis of threo-4,5-dihydroxy diastereomers of sphinganine(1975)
- Study on the behaviors of Na-KOH/γ-Al_2O_3 solid superbase catalyst(2004)