Low Pressure Catalytic Hydrogenation of Nitroparaffins

Iffland, Don C.; Cassis, Frank A.

doi:10.1021/ja01144a511

Cited by 8 publications

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“…The use of nickel borohydride gave unreacted starting material among a mixture of degradation products. Hydrogenolysis with Pt/H 2 or with Raney nickel alone gave recovered starting material. Raney nickel reduction in the presence of atmospheric H 2 gave only ∼10% reduced product along with recovered starting material after 24 h .…”

Section: Resultsmentioning

confidence: 99%

Scope and Limitations of the Nitro-Mannich Reaction for the Stereoselective Synthesis of 1,2-Diamines

et al. 2004

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The acetic acid-promoted addition of lithium nitropropanate and the Lewis acid-catalyzed [Sc(OTf)3, Cu(OTf)2, or Ti(OiPr)4] addition of trimethylsilyl nitropropanate to a range of heteroaromatic and simple aliphatic aldimines gave anti-rich (approximately 3-19:1) beta-nitroamines in >95% yields as the kinetic products. It was found that a nonpolar N-imine protecting group was essential for reactivity with the o-methoxybenzyl (OMB) group giving better selectivities and yields than p-methoxybenzyl (PMB) or p-methoxyphenyl (PMP) in the Lewis acid-catalyzed addition reactions. Reduction with SmI2, treatment with COCl2, followed by OMB deprotection gave diastereomerically pure cis-imidazolidinones in 55-79% overall yield from imine. Preliminary results have shown that acetic acid can catalyze the reaction of N-OMB-benzylideneamine with nitropropane, used as solvent, to give the thermodynamically more stable syn-beta-nitroamine product.

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Section: Resultsmentioning

confidence: 99%