913638-29-6Relevant academic research and scientific papers
Copper-Nitrene-Catalyzed Desymmetric Oxaziridination/1,2-Alkyl Rearrangement of 1,3-Diketones toward Bicyclic Lactams
Han, Xue,Shan, Li-Xin,Tu, Yong-Qiang,Wang, Hong,Yang, Ming,Zhang, Chang-Sheng,Zhang, Fu-Min,Zhang, Wen-Shuo,Zhang, Xiao-Ming,Zhu, Jin-Xin
supporting information, p. 22688 - 22692 (2021/09/18)
Although copper-nitrene has been extensively studied as a versatile active species in various transformations, asymmetric reactions involving copper-nitrene have been limited to the aziridination of olefins. Herein, we report the novel copper-nitrene-catalyzed desymmetric oxaziridination reaction of cyclic diketones with alkyl azides and the subsequent rearrangement of the resulting highly active intermediate, which produces a synthetically challenging chiral bicyclic lactam containing a quaternary carbon center. This procedure not only enriches the copper-nitrene-catalyzed asymmetric reactions, but also provides an alternative strategy to address the inherent challenges of catalytic asymmetric Schmidt reactions. This unique reaction could inspire the investigation of novel copper-nitrene-catalyzed asymmetric transformations and their reaction mechanisms.
Chiral Bronsted acid-promoted enantioselective desymmetrization in an intramolecular schmidt reaction of symmetric azido 1,3-hexanediones: Asymmetric synthesis of azaquaternary pyrroloazepine skeletons
Yang, Ming,Zhao, Yu-Ming,Zhang, Shu-Yu,Tu, Yong-Qiang,Zhang, Fu-Min
supporting information, p. 1344 - 1347 (2013/01/11)
The enantioselective desymmetrization of 2-substituted-2-azidopropyl 1,3-hexanediones through an asymmetric intramolecular Schmidt reaction using a chiral Bronsted acid has been developed for the first time. Synthetically interesting pyrroloazepine skeletons with an azaquaternary stereogenic center with up to 59 % ee are accessed effectively (see scheme; R=H, alkyl, or aryl). Copyright
Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1,3-diketones
Lertpibulpanya, Duanpen,Marsden, Stephen P.
, p. 3498 - 3504 (2008/09/16)
Readily prepared 2-alkyl-2-azidopropylcycloalkyl-1,3-diones undergo intramolecular Schmidt rearrangement with a range of hard Lewis acids, leading to indolizidinediones and pyrroloazepinediones. Chiral aluminium-based Lewis acids could also be used to mediate this symmetry-breaking transformation, but no significant asymmetric induction was observed. The Royal Society of Chemistry 2006.
