52784-31-3Relevant articles and documents
Scott,Minton
, p. 411 (1977)
Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams
Sietmann, Jan,Ong, Mike,Mück-Lichtenfeld, Christian,Daniliuc, Constantin G.,Wiest, Johannes M.
supporting information, p. 9719 - 9723 (2021/03/16)
Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.
Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2
Xing, Qingzhao,Hao, Zhe,Hou, Jing,Li, Gaoqiang,Gao, Ziwei,Gou, Jing,Li, Chaoqun,Yu, Binxun
, p. 9563 - 9586 (2021/07/20)
Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.