More Like this

1. Photoinduced α-Cleavage of 2-Azido-2-phenyl-1,3-indandione at Cryogenic Temperatures

   https://doi.org/10.1021/acs.orglett.0c02794  

   Banerjee, Upasana; Sarkar, Sujan K.; Krause, Jeanette A.; Karney, William L.; Abe, Manabu; Gudmundsdottir, Anna D. (October 2020, Organic Letters)
2. Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks

   https://doi.org/10.1016/j.carres.2019.107900  

   Alex, Catherine; Visansirikul, Satsawat; Zhang, Yongzhen; Yasomanee, Jagodige P.; Codee, Jeroen; Demchenko, Alexei V. (February 2020, Carbohydrate Research)
3. Photolysis of 5-Azido-3-Phenylisoxazole at Cryogenic Temperature: Formation and Direct Detection of a Nitrosoalkene

   https://doi.org/10.3390/molecules25030543  

   Banerjee, Upasana; Karney, William L.; Ault, Bruce S.; Gudmundsdottir, Anna D. (February 2020, Molecules)

   To enhance the versatility of organic azides in organic synthesis, a better understanding of their photochemistry is required. Herein, the photoreactivity of azidoisoxazole 1 was characterized in cryogenic matrices with IR and UV-Vis absorption spectroscopy. The irradiation (λ = 254 nm) of azidoisoxazole 1 in an argon matrix at 13 K and in glassy 2-methyltetrahydrofuran (mTHF) at 77 K yielded nitrosoalkene 3. Density functional theory (DFT) and complete active space self-consistent field (CASSCF) calculations were used to aid the characterization of nitrosoalkene 3 and to support the proposed mechanism for its formation. It is likely that nitrosoalkene 3 is formed from the singlet excited state of azidoisoxazole 1 via a concerted mechanism or from cleavage of an intermediate singlet nitrene that does not undergo efficient intersystem crossing to its triplet configuration. 

   more » « less
4. Bromine‐Promoted Glycosidation of Conformationally Superarmed Thioglycosides

   https://doi.org/10.1002/chem.201901969  

   Panza, Matteo; Civera, Monica; Yasomanee, Jagodige P.; Belvisi, Laura; Demchenko, Alexei V. (August 2019, Chemistry – A European Journal)
5. Ferric Chloride Promoted Glycosidation of Alkyl Thioglycosides

   https://doi.org/10.3390/molecules29204845  

   Ridgway, Lacie M; Das, Anupama; Shadrick, Melanie L; Demchenko, Alexei V (October 2024, Molecules)

   Reported herein is a new reaction for glycosylation with thioglycosides in the presence of iron(III) chloride. Previously, FeCl3 was used for the activation of thioglycosides as a Lewis acid co-promoter paired with NIS. In the reported process, although 5.0 equiv of FeCl3 are needed to activate thioglycosides most efficiently, no additives were used, and the reactions with reactive glycosyl donors smoothly proceeded to completion in 1 h at 0 °C. This work showcases a new direction in developing glycosylation methods using greener and earth-abundant activators. 

   more » « less