1613406-81-7Relevant articles and documents
Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction
Feng, Chen-Guo,Xu, Si-Yu,Zhang, Rui,Zhang, Shu-Sheng
, p. 4492 - 4496 (2021/05/31)
A nickel-catalyzed asymmetric Suzuki-Miyaura cross-coupling of racemic 3-bromo-phthalides and arylboronic acids was realized for the synthesis of diverse chiral 3-aryl-phthalides in moderate to excellent reaction yields. The reaction proceeded in a stereoconvergent manner and high enantioselectivities were observed for most examined examples. A number of functional groups like aldehyde, ester and bromide were well tolerated. Heteroaromatic boronic acids were also competent coupling partners in this reaction.
Rhodium(III)-Catalyzed Asymmetric Addition of Inert Arene C-H Bond to Aldehydes to Afford Enantioenriched Phthalides
Chen, Wenkun,Li, Jie,Xie, Hui,Wang, Jun
supporting information, p. 3586 - 3590 (2020/04/20)
An asymmetric rhodium(III)-catalyzed Grignard-type addition of inert arene C-H bond to aldehydes is reported. It provides a new strategy for the synthesis of chiral 3-substituted phthalides in good yields (up to 87%) with high enantiomeric purity (up to 99% ee). Interestingly, a chiral-matching effect between substrate and catalyst was observed, which is crucial to accomplish satisfied reaction outcomes. Mechanistically, the reaction is assumed to proceed via consecutive C(sp2)-H activation of benzamide, addition to aldehyde, and lactonization.
Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins
Yang, Junfeng,Yoshikai, Naohiko
, p. 16748 - 16751 (2015/02/05)
Cobalt-chiral diphoshine catalytic systems promote intramolecular hydroacylation reactions of 2-acylbenzaldehydes and 2-alkenylbenzaldehydes to afford phthalide and indanone derivatives, respectively, in moderate to good yields with high enantioselectivities. The ketone hydroacylation did not exhibit a significant H/D kinetic isotope effect (KIE) with respect to the aldehyde C-H bond, indicating that C-H activation would not be involved in the rate-limiting step.
