1,2-Amino Alcohols via Cr/Photoredox Dual-Catalyzed Addition of α‑Amino Carbanion Equivalents to Carbonyls

Herein, we report
the synthesis of protected 1,2-amino alcohols
starting from carbonyl compounds and α-silyl amines. The reaction
is enabled by a Cr/photoredox dual catalytic system that allows the in situ generation of α-amino carbanion equivalents
which act as nucleophiles. The unique nature of this reaction was
demonstrated through the aminoalkylation of ketones and an acyl silane,
classes of electrophiles that were previously unreactive toward addition
of alkyl-Cr reagents. Overall, this reaction broadens the scope of
Cr-mediated carbonyl alkylations and discloses an underexplored retrosynthetic
strategy for the synthesis of 1,2-amino alcohols.