54808-41-2Relevant academic research and scientific papers
Multicomponent cis- and trans-Aziridinatons in the Syntheses of All Four Stereoisomers of Sphinganine
Zhou, Yubai,Mukherjee, Munmun,Gupta, Anil K.,Wulff, William D.
, p. 2230 - 2233 (2017)
All four stereoisomers of sphinganine can be synthesized by a multicomponent aziridination of an aldehyde, an amine and an α-diazo carbonyl compound mediated by a BOROX catalyst with high asymmetric induction (≥96% ee). The threo isomers are available from ring-opening of cis-aziridines by an oxygen nucleophile with inversion at the C-3 position and the erythro-isomers are likewise available from trans-aziridines.
Attempted Synthesis of a Stable, Quintet, Tetraphenoxyl Tetraradical: Facile Rearrangement of a Substituted Bicyclobutane
Anderson, Kraig K.,Shultz, David A.,Dougherty, Dennis A.
, p. 7575 - 7584 (2007/10/03)
The preparation of tetraphenol 3 and its attempted oxidation to tetraradical 2 are described. Tetraphenoxyl 2 was envisioned as a more stable analog of the previously reported, quintet tetraradical 1. However, EPR studies on 3 and model compounds and crystallographic characterization of the product from oxidation of 3 suggest that 2 is not a viable target. Apparently, 2 or an intermediate in the multistep oxidation path leading to it undergoes a ring closure to a bicyclobutane. The bicyclobutane, in turn, undergoes a surprisingly facile rearrangement to the analogous butadiene structure.
