A Unified Approach to the Aminoallylation of Carbonyl Compounds Through Cu-Catalyzed Enantioselective Reductive Coupling of Allenamides

17 November 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Herein, we report the development of a highly enantioselective aminoallylation reaction of both aldehyde and ketone electrophiles through the Cu-catalyzed reductive coupling of N-substituted allenes (allenamides). Through optimization of the allenamide to avoid an on-cycle rearrangement, high enantioselectivities could be obtained for a variety of ketone and aldehyde electrophiles in up to >99% ee and >98:2 anti:syn diastereoselectivities. Use of the acyclic allenamides described in this report selectively generated anti-diastereomers in contrast to cyclic allenamides that were previously shown to favor the syn form. Rationale for this change in diastereoselectivity and synthetic applications are also presented.


reductive coupling
copper catalysis


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