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Gold-catalyzed imination/Mannich reaction cascades on readily available 3-en-1-ynamides enable the diastereoselective synthesis of 1,5-iminoamino compounds in a one-pot operation. The reactions work well with diversified 3-en-1-ynamides, aldehydes and anilines with good to excellent diastereoselectivities. Our control experiments indicate gold-catalyzed aminations of 3-en-1-ynamides to yield α-imino allylgold intermediates that react subsequently with iminiums to implement the Mannich reactions stereoselectively. The reactions proceed with anti-selectivity for those 3-en-1-ynamides bearing acyclic alkenes whereas syn-selectivity is seen for their cycloalkene-based analogues. An open-transition state can satisfactorily rationalize these observed stereoselectivities based on an antiperiplanar conformation. [ABSTRACT FROM AUTHOR]

The article presents chemical equation for the article "Gold-Catalyzed Imination/Mannich Reaction Cascades of 3-En-1-ynamides with Anilines and Aldehydes to Enable 1,5-Nitrogen Functionalizations" by R. R. Singh and others, published in the journal "Advanced Synthesis & Catalysis" in 2016.