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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.
Triallylborane-amine adducts can be used as stoichiometric allylating
agents for efficient aminoallylation reactions of carbonyl compounds in methanol.
Moreover, copper catalysis enables a diastereoselective allylation of Ellman’s
imine.
N. Y. Kuznetsov, R. M. Tikhov, T. V. Strelkova, Y. N. Bubnov, Org. Lett.,
2018, 20, 3549-3552.
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.
