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Synthesis of homoallylic amines

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A three-component condensation of aldehydes, benzyl carbamate and allyltrimethylsilane, which affords corresponding protected homoallylic amines in excellent yields, is catalyzed by iodine.
P. Phukan, J. Org. Chem., 2004, 69, 4005-4006.


A palladium complex catalyzes two transformations in one pot: formation of allylsilane from allyl trifluoroacetate using hexamethyldisilane and subsequent imine allylation. A three-component reaction was developed where preformed imines were replaced with aldehydes and anisidine. Under these reaction conditions various aldehydes react smoothly to afford homoallylic amines.
R. E. Grote, E. R. Jarvo, Org. Lett., 2009, 11, 485-488.


A copper-catalyzed ring-opening hydroamination of methylenecyclopropanes with polymethylhydrosiloxane and O-benzoylhydroxylamines provides homoallylamines in very good yields. The cyclopropane C-C bond cleavage occurs selectively at the more congested proximal position.
D. Nishikawa, R. Sakae, Y. Miki, K. Hirano, M. Miura, J. Org. Chem., 2016, 81, 12128-12134.


A convenient and efficient method for aminobromination of alkylidenecyclopropanes is reported. This is exemplified in the stereoselective preparation of N-[(Z)-3-bromobut-3-en-1-yl]-p-toluenesulfonamides by using p-toluenesulfonamide and N-bromosuccinimide (NBS) as nitrogen and bromine sources, respectively.
X. Huang, W.-J. Fu, Synthesis, 2006, 1016-1017.