Herein, we report the first Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. Key for success was the discovery of a new sterically encumbered bis(oxazoline) ligand backbone, thus offering a de novo technology for accessing enantioenriched sp 3 −sp 3 linkages via sp 3 C−N functionalization. Our protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization. In addition, an enantioselective deaminative remote hydroalkylation reaction of unactivated internal olefins is within reach, thus providing a useful entry point for forging enantioenriched sp 3 −sp 3 centers at remote sp 3 C−H sites.
A C-3
aminolysis of epoxy homoallylic alcohols has been accomplished,
which was catalyzed by a commercially available boronic acid. Due
to the directing effect of the hydroxyl moiety, the ring opening reaction
of a variety of 3,4-epoxy alcohols bearing different substitution
patterns with various aromatic amines as nucleophiles proceeded in
a stereospecific reaction pathway at the C-3 position furnishing various
amino alcohols as products in a highly regioselective manner.
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