1078160-20-9Relevant articles and documents
Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of α-Tertiary Amino Ketones from Sulfonium Ylides
Guo, Wengang,Li, Pingfan,Luo, Yuzheng,Sun, Jianwei,Sung, Herman H.-Y.,Williams, Ian D.
, p. 14384 - 14390 (2020/09/15)
Herein we disclose a new catalytic asymmetric approach for the synthesis of chiral α-Amino ketones, which is particularly useful for the less accessible acyclic α-Tertiary cases. By a protonation-Amination sequence, our approach represents a rare asymmetric H-heteroatom bond insertion by α-carbonyl sulfonium ylides, an attractive surrogate of diazocarbonyls. The mild intermolecular C-N bond formation was catalyzed by chiral phosphoric acids with excellent efficiency and enantioselectivity. The products are precursors to other important chiral amine derivatives, including drug molecules and chiral ligands. The enantioselectivity was controlled by dynamic kinetic resolution in the amination step, rather than the initial protonation. This process opens up a new platform for the development of other related insertion reactions.
N-Arylazetidines: Preparation through Anionic Ring Closure
Quinodoz, Pierre,Drouillat, Bruno,Wright, Karen,Marrot, Jéro?me,Couty, Fran?ois
, p. 2899 - 2910 (2016/04/26)
We report herein an efficient synthesis of diversely substituted N-aryl-2-cyanoazetidines based on an anionic ring-closure reaction. These compounds can be prepared from β-amino alcohols in enantiomerically pure form through a three-step sequence involving (i) copper-catalyzed N-arylation, (ii) N-cyanomethylation of the secondary aniline, and (iii) one-pot mesylation followed by ring closure induced by a base. This high-yielding sequence gives access to azetidines with a predictable and adjustable substitution pattern and also with predictable diastereoselectivity. These compounds are susceptible to multiple further derivatizations through Suzuki coupling or nitrile transformation, thus appearing as valuable new scaffolds for medicinal chemistry. Their rigid shape, featuring an almost planar N-arylamine and a planar four-membered ring, was revealed by both AM1 calculations and X-ray crystallography.
