J. L. Schwarz, Roman Kleinmans, Tiffany O. Paulisch
Jan 10, 2020
Citations
0
Influential Citations
59
Citations
Journal
Journal of the American Chemical Society
Abstract
Herein, we report the synthesis of protected 1,2-amino alcohols starting from carbonyl compounds (mostly aldehydes) 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 towards addition of alkyl-Cr reagents. Overall this reaction broadens the scope of Cr-mediated carbonyl alkylations and discloses an underex-plored retrosynthetic strategy for the synthesis of 1,2-amino alcohols.