36081-66-0Relevant articles and documents
Rh-Catalyzed Chemoselective [4 + 1] Cycloaddition Reaction toward Diverse 4-Methyleneprolines
Cai, Wangshui,Wu, Junxian,Zhang, Haowei,Jalani, Hitesh B.,Li, Guigen,Lu, Hongjian
, p. 10877 - 10891 (2019)
An efficient synthesis of 4-methyleneproline derivatives has been developed through an Rh-catalyzed [4 + 1] cycloaddition strategy using 3-methyleneazetidines and diazo compounds. The reaction proceeds under very mild conditions with a high degree of chemoselectivity, and competing experiments revealed that it is the preferred reaction, dominant over the C-H insertion, O-H insertion, and olefin cyclopropanation reactions which are commonly observed in Rh carbene chemistry. This method can incorporate the proline ester scaffold in pharmaceuticals and natural products. The intramolecular version of the reaction effectively provides proline-fused small to medium-sized tricyclic heterocycles. Gram-scale reactions, one-time addition of diazo compounds, and a minimum catalyst loading of 0.1 mol %, proceeded smoothly, implying their practicality.
Visible-Light-Promoted [3 + 2] Cycloaddition of 2H-Azirines with Quinones: Access to Substituted Benzo[f]isoindole-4,9-diones
Wang, Lijia,Liu, Chuang,Li, Lei,Wang, Xin,Sun, Ran,Zhou, Ming-Dong,Wang, He
supporting information, p. 719 - 724 (2022/01/22)
A visible-light-promoteded [3 + 2] cycloaddition reaction of 2H-azirines with quinones has been developed under mild reaction conditions. The reaction provides a general and efficient strategy for the synthesis of the benzo[f]isoindole-4,9-diones scaffold
Asymmetric Synthesis of 1,2-Dihydronaphthalene-1-ols via Copper-Catalyzed Intramolecular Reductive Cyclization
Acharyya, Ranjan Kumar,Kim, Soyoung,Park, Yeji,Han, Jung Tae,Yun, Jaesook
, p. 7897 - 7902 (2020/11/02)
We describe a copper-catalyzed intramolecular reductive cyclization of easily accessible benz-tethered 1,3-dienes containing a ketone moiety. This process provided biologically active 1,2-dihydronaphthalene-1-ol derivatives in good yields with excellent enantio- and diastereoselectivity. Mechanistic investigations using density functional theory revealed that (Z)- and (E)-allylcopper intermediates formed in situ from the diene and copper catalyst undergo isomerization and selective intramolecular allylation of the (E)-allylcopper form of the major product through a six-membered boatlike transition state. The resulting products were further transformed to fully saturated naphthalene-1-ols by reactions of the olefin moiety.
