42718-20-7Relevant academic research and scientific papers
Synthesis of 3-Hydroxymethyl Isoindolinones via Cobalt-Catalyzed C(sp2)-H Carbonylation of Phenylglycinol Derivatives
Lukasevics, Lukass,Cizikovs, Aleksandrs,Grigorjeva, Liene
supporting information, p. 2720 - 2723 (2020/03/30)
An efficient method for the synthesis of 3-hydroxymethyl isoindolinones via cobalt-catalyzed C(sp2)-H carbonylation of phenylglycinol derivatives using picolinamide as a traceless directing group is demonstrated. The reaction proceeds in the presence of a commercially available cobalt(II) tetramethylheptanedionate catalyst and employs DIAD as a "CO" surrogate. This synthetic route offers a broad substrate scope, excellent regioselectivity, and full preservation of the original stereochemistry. Besides, the developed method provides a pathway for accessing valuable enantiopure 3-substituted isoindolinone derivatives.
Cobalt-Catalyzed, Directed C-H Functionalization/Annulation of Phenylglycinol Derivatives with Alkynes
Bolsakova, Jekaterina,Lukasevics, Lukass,Grigorjeva, Liene
, p. 4482 - 4499 (2020/04/09)
A new method for cobalt-catalyzed C(sp2)-H functionalization of phenylglycinol derivatives with terminal and internal alkynes directed by picolinamide auxiliary has been developed. This method offers an efficient and highly regioselective route for the synthesis of 1-hydroxymethyltetrahydroisoquinolines. The reaction employs commercially available Co(II) catalyst in the presence of Mn(III) cooxidant and oxygen as a terminal oxidant and proceeds with full preservation of original stereochemistry.
Triple role of phenylselenonyl group enabled a one-pot synthesis of 1,3-oxazinan-2-ones from α-isocyanoacetates, phenyl vinyl selenones, and water
Buyck, Thomas,Wang, Qian,Zhu, Jieping
supporting information, p. 11524 - 11528 (2014/10/15)
Reaction of α-substituted α-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.
Efficient access to (1H)-isoindolin-1-one-3-carboxylic acid derivatives by orthopalladation and carbonylation of methyl arylglycinate substrates
Nieto, Sonia,Sayago, Francisco J.,Laborda, Pedro,Soler, Tatiana,Cativiela, Carlos,Urriolabeitia, Esteban P.
, p. 4185 - 4191 (2011/07/08)
The orthopalladation of methyl arylglycinate derivatives has been studied. The reaction proceeds efficiently for different electron-withdrawing and electron-releasing substituents at the aryl ring. The carbonylation of the orthopalladated complexes affords, in a single step, substituted (1H)-isoindolin-1-one-3-carboxylates. These compounds constitute valuable synthetic intermediates and can be transformed diastereoselectively into octahydroisoindole-1-carboxylic acid derivatives, an important scaffold in the synthesis of many biologically active compounds.
