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- W3201970921 abstract "This article discloses the direct α-amination of α-branched aldehydes applying nitrogen-based nucleophiles. Under organocatalyzed, oxidative conditions α-branched aldehydes are umpoled to their electrophilic synthons and, subsequently, displaced by a variety of nucleophilic amines to form tetrasubstituted tertiary centers. A similar strategy has been previously employed to form congested C-C, C-O, and C-S bonds; however, unsatisfactory results were received when extending the methodology to include C-N bonds. Initially, intramolecular α-amination reactions were undertaken to foster dihydroquinoxaline-type products. A solvent exchange to the polar, aprotic solvent, MeNO2, proved critical to facilitate intermolecular α-C-N bond formation with a wide range of amine coupling partners (N-heterocycles, N,N-diaryl amines, and anilines). Application of the solvent exchange to the enantioselective SN2-DKR manifold provided distinct regimes leading to refinement in yield and enantioselectivity." @default.
- W3201970921 created "2021-10-11" @default.
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- W3201970921 date "2021-10-05" @default.
- W3201970921 modified "2023-10-01" @default.
- W3201970921 title "Metal-free, Oxidative α-Coupling of Aldehydes with Amine Nucleophiles for the Preparation of Congested C(sp<sup>3</sup>)–N Bonds" @default.
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- W3201970921 doi "https://doi.org/10.1021/acs.joc.1c01937" @default.
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