Ruthenium–NHC–Diamine Catalyzed Enantioselective Hydrogenation of Isocoumarins
作者:Wei Li、Mario P. Wiesenfeldt、Frank Glorius
DOI:10.1021/jacs.6b13124
日期:2017.2.22
A novel and practical chiral ruthenium-NHC-diamine system is disclosed for the enantioselective hydrogenation of isocoumarins, which provides a new concept to apply (chiral) NHC ligands in asymmetriccatalysis. A variety of optically active 3-substituted 3,4-dihydroisocoumarins were obtained in excellent enantioselectivities (up to 99% ee). Moreover, this methodology was utilized in the synthesis of
Synthesis of Isocoumarin Derivatives via the Copper-Catalyzed Tandem Sequential Cyclization of 2- Halo-<i>N</i>-phenyl Benzamides and Acyclic 1,3-Diketones
作者:Veerababurao Kavala、Cheng-Chuan Wang、Deepak Kumar Barange、Chun-Wei Kuo、Po-Min Lei、Ching-Fa Yao
DOI:10.1021/jo300501j
日期:2012.6.1
A facile and rapid synthesis of isocoumarin derivatives using a copper-catalyzed tandem C–C/C–O coupling strategy from readily available substrates is described. The reactions of a wide range of 2-iodo-N-phenyl benzamides and acyclic diketones as starting materials were investigated.
Assembly of 3-Substituted Isocoumarins via a CuI-Catalyzed Domino Coupling/Addition/Deacylation Process
作者:Shangjun Cai、Fei Wang、Chanjuan Xi
DOI:10.1021/jo2026433
日期:2012.3.2
An efficient strategy for the synthesis of a variety of 3-substitutedisocoumarins has been developed. The reaction proceeded from o-halobenzoic acids and 1,3-diketones via a copper(I)-catalyzed domino reaction in DMF under the action of K3PO4 at 90–120 °C without a ligand to afford the corresponding 3-substitutedisocoumarin derivatives in good to excellent yields. o-Halobenzoic acids could be o-iodobenzoic
已经开发了用于合成多种3-取代的异香豆素的有效策略。该反应由邻卤代苯甲酸和1,3-二酮经DMF中的铜(I)催化的多米诺反应,在K 3 PO 4的作用下于90-120°C下进行,没有配体,得到相应的3-取代的异香豆素衍生物的收率为好至极好。邻卤代苯甲酸可以是邻碘苯甲酸,邻溴苯甲酸和邻氯苯甲酸衍生物。1,3-二酮可以是烷基和芳基取代的1,3-二酮。
Tandem Reactions Leading to Benzo[c]chromen-6-ones and 3-Substituted Isocoumarins
A simple and convenient protocol for the synthesis of benzo[c]chromen-6-ones and 3-substitutedisocoumarins through a CuI-catalyzed tandemreaction of 2-bromobenzoates withcyclohexane-1,3-diones or acyclic 1,3-diones is developed. This strategy can also be extended to the one-pot synthesis of isoquinolin-1(2H)-one and 3,4-dihydrophenanthridine-1,6(2H,5H)-dione.