911213-98-4Relevant 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.
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.
Asymmetric aza-Wittig reactions: Enantioselective synthesis of β-quaternary azacycles
Lertpibulpanya, Duanpen,Marsden, Stephen P.,Rodriguez-Garda, Ignacio,Kilner, Colin A.
, p. 5000 - 5002 (2007/10/03)
A hindrance no more: The direct asymmetric synthesis of nitrogen heterocycles containing β-quaternary stereocenters, widely found for example in alkaloids, is highly challenging. The novel approach shown exploits the desymmetrization of prochiral diketo azides to unmask the asymmetric quaternary center, and represents the first reported examples of the asymmetric aza-Wittig reaction. (Chemical Equation Presented).
