A mild
and convenient process for direct transformation of nitroalkanes
to the corresponding nitriles was developed using a visible-light
photoredox catalysis strategy with household decorative blue LEDs
and the additives of Et3N and DIPIBA (or DIPEA). Application
of the process in secondary nitroalkanes bearing a β-alcohol
resulted in a domino process of the retro-Henry reaction and the subsequent
acetalization, aldol, cyanohydrin, and ring-contraction reactions
with stereoselectivities. The photocatalytic reaction was demonstrated
by a continuous flow method.
Efficient construction of Hajos–Parrish-type ketones with six contiguous stereogenic centers in a formal [2 + 2 + 2] cycloaddition cascade. The spontaneous resolution of racemic product without the need for chiral agent has been achieved.
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