320575-05-1Relevant academic research and scientific papers
Towards the total synthesis of tonantzitlolone - Preparation of key fragments and the complete carbon backbone
Wittenberg, Rüdiger,Beier, Christian,Dr?ger, Gerald,Jas, Gerhard,Jasper, Christian,Monenschein, Holger,Kirschning, Andreas
, p. 4457 - 4460 (2007/10/03)
The first synthetic advances towards the novel diterpenoid tonantzitlolone 1 are described. The key steps in the synthesis involve a chromium(II) Reformatsky reaction, a diastereoselective C1 extension and an expeditious aldol coupling step of
Polymer-Supported Bisacetoxybromate(I) Anion - An Efficient Co-Oxidant in the TEMPO-Mediated Oxidation of Primary and Secondary Alcohols
Bruenjes, Marco,Sourkouni-Argirusi, Georgia,Kirschning, Andreas
, p. 635 - 642 (2007/10/03)
A polymer-bound reagent for the efficient oxidation of primary alcohols to aldehydes and secondary alcohols to ketones in the presence of a catalytic amount of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) is described. The oxidation process is particular mild and allows one to prepare aldehydes with α-chirality without racemization. This also includes the synthesis of α-aminoaldehydes. In most cases, work-up of this heavy metal-free oxidation is achieved by simple filtration followed by removal of the solvent. Insight into the role of the bromate(I) anion in the oxidation process was gained from the TEMPO-mediated oxidation of benzaldehyde in the presence of the hypochlorite anion loaded on an anion exchange resin.
A New Polymer-attached Reagent for the Oxidation of Primary and Secondary Alcohols
Sourkouni-Argirusi, Georgia,Kirschning, Andreas
, p. 3781 - 3784 (2007/10/03)
formula presented A new, polymer-bound reagent system for the efficient oxidation of primary alcohols to aldehydes and secondary alcohols to ketones in the presence of a catalytic amount of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) is described. In most cases, workup of this heavy metal-free oxidation is achieved by simple filtration followed by removal of the solvent. In selected examples this reagent was compared with the known polymer-bound permanganate and chromium(VI) reagents.
