1279712-69-4Relevant academic research and scientific papers
Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey–Seebach Reaction
Crespi, Stefano,Donabauer, Karsten,K?nig, Burkhard,Murugesan, Kathiravan,Rozman, Ur?a
, p. 12945 - 12950 (2020/09/23)
A metal-free generation of carbanion nucleophiles is of prime importance in organic synthesis. Herein we report a photocatalytic approach to the Corey–Seebach reaction. The presented method operates under mild redox-neutral and base-free conditions giving the desired product with high functional group tolerance. The reaction is enabled by the combination of photo- and hydrogen atom transfer (HAT) catalysis. This catalytic merger allows a C?H to carbanion activation by the abstraction of a hydrogen atom followed by radical reduction. The generated nucleophilic intermediate is then capable of adding to carbonyl electrophiles. The obtained dithiane can be easily converted to the valuable α-hydroxy carbonyl in a subsequent step. The proposed reaction mechanism is supported by emission quenching, radical–radical homocoupling and deuterium labeling studies as well as by calculated redox-potentials and bond strengths.
New synthetic strategy for high-enantiopurity N-protected α-amino ketones and their derivatives by asymmetric hydrogenation
Sun, Tian,Hou, Guohua,Ma, Miaofeng,Zhang, Xumu
, p. 253 - 256 (2011/04/16)
Asymmetric hydrogenation of α-dehydroamino ketones catalyzed by a rhodium-chiral phosphorus ligand complex (up to 99% ee, 1000 TON), represents an efficient approach to chiral α-amino ketones. The reduction of α-amino ketones catalyzed by palladium on carbon (Pd/C) leads to amphetamine precursors with quantitative yield and no significant enantioselectivity loss.
