1015248-96-0Relevant articles and documents
Kinetic analysis of the HBTM-catalyzed esterification of an enantiopure secondary alcohol
Wagner, Alexander J.,Rychnovsky, Scott D.
, p. 5504 - 5507 (2013)
A detailed kinetic analysis of the homobenzotetramisole-mediated esterification of the enantiopure secondary alcohol (1R,2S)-2-phenylcyclohexanol is presented. The results of this analysis show that the reaction is first order in the homobenzotetramisole catalyst, first order in (1R,2S)-2- phenylcyclohexanol, and first order in propionic anhydride. Initial rates, the turnover frequency of the catalyst, and different excess plots were utilized in this evaluation. Additionally, a same excess plot revealed no noticeable catalyst decomposition or product inhibition during the course of the reaction.
Concise synthesis of the isothiourea organocatalysts homobenzotetramisole and derivatives
Ranieri, Beatrice,Robles, Omar,Romo, Daniel
supporting information, p. 6291 - 6296 (2013/07/25)
A concise approach to the synthesis of homobenzotetramisole and derivatives is described. Our strategy features a one-pot acylation-cyclization of 2-aminobenzothiazole with α,β-unsaturated acid chlorides to afford annulated pyrimidones. Subsequent Grignard addition followed by acid-promoted dehydration and reduction provides good overall yields of the title compounds in three steps and in quantities up to 10 g. The synthesis employs low-cost and readily available starting materials and enables access to both optical antipodes of these increasingly useful nucleophilic catalysts following chiral separation.
Nucleophilicities and Lewis basicities of isothiourea derivatives
Maji, Biplab,Joannesse, Caroline,Nigst, Tobias A.,Smith, Andrew D.,Mayr, Herbert
supporting information; experimental part, p. 5104 - 5112 (2011/08/06)
Rate and equilibrium constants for the reactions of a series of isothioureas with benzhydrylium ions have been measured photometrically. The data were employed to determine the nucleophilicities and nucleofugalities of isothioureas and compare them with t