233751-75-2Relevant academic research and scientific papers
Positional chemoselectivity in the Zn(II)-mediated removal of phenol protecting groups
Fleury, Lauren M.,Gianino, Joseph B.,Ashfeld, Brandon L.
supporting information, p. 5376 - 5379 (2012/10/30)
A protocol was developed for the chemoselective ortho-deprotection of polyphenolic substrates using readily available ZnIIX2 salts. This procedure provides exceptional positional selectivity for the deprotection of phenols that reside adjacent to directing carbonyl functionality in the presence of similar protecting groups at the meta and para positions. Good to excellent yields of the desired free phenols were obtained (≤96%), and a wide assortment of protecting groups was readily removed under the reaction conditions.
Selective cleavage of tert-butyldimethylsilylethers ortho to a carbonyl group by ultrasound
De Groot, Alex H.,Dommisse, Roger A.,Lemière, Guy L.
, p. 1541 - 1549 (2007/10/03)
A general method for the selective cleavage of tert- butyldimethylsilylethers ortho to a carbonyl group is established by sonication of a 0.1 M solution of the substrate in 1/1 (v/v) CH3OH/CCl4. Other phenolic tert-butyldimethylsilylethers are unaffected. This reaction performed on flavanoids is completed within 3 h and no special workup is required. Other substrates are also investigated and a mechanism is proposed. (C) 2000 Elsevier Science Ltd.
Metallated 2-alkenyl sulfoximines in asymmetric synthesis: Regio- and stereoselective synthesis of highly substituted oxabicyclic ethers and studies towards the total syntheses of the euglobals G1 and G2 and arenaran A
Reggelin, Michael,Gerlach, Matthias,Vogt, Melanie
, p. 1011 - 1031 (2007/10/03)
2-Cyclopentenyl- and 2-cyclohexenylmethyl sulfoximines can be converted into angular carbon-functionalised, highly substituted, isomerically pure (ds ± 98%) 2-oxabicyclo[3.3.0]octanes and 2-oxabicyclo[3.4.0]nonanes in high yields by a convenient one-pot sequence. Molecular frameworks such as these can be found in many biologically active natural products. In addition to the methodological work, we report on studies towards the total synthesis of the euglobals G1 and G2 and arenaran A.
