1610366-32-9Relevant articles and documents
Enantioselective Oxidation of Alkenes with Potassium Permanganate Catalyzed by Chiral Dicationic Bisguanidinium
Wang, Chao,Zong, Lili,Tan, Choon-Hong
supporting information, p. 10677 - 10682 (2015/09/28)
Chiral anion-controlled ion-pairing catalysis was demonstrated to be a wide-ranging strategy that can utilize a variety of cationic metal species. In a similar manner, we envision a complementary strategy using chiral cation in partnership with inorganic anionic metal salts. Herein, we report a chiral dicationic bisguanidinium-catalyzed asymmetric oxidation reaction of alkenes with potassium permanganate. Chiral induction is attributed to ion-pairing interaction between chiral cation and enolate anion. The success of the current permanganate oxidation reaction together with mechanistic insights should provide inspiration for expansion to other anionic metal salts and would open up new paradigms for asymmetric transition metal catalysis, phase-transfer catalysis, and ion-pairing catalysis.
Total synthesis of a reported fluorometabolite from Streptomyces sp. TC1 indicates an incorrect assignment. the isolated compound did not contain fluorine
Ayoup, Mohammed Salah,Cordes, David B.,Slawin, Alexandra M. Z.,O'Hagan, David
, p. 1249 - 1251 (2014/07/21)
3,5-Di-tert-butyl-4-fluorophenylpropionic acid (1) was recently reported as a natural product from Streptomyces sp. TC1. This was a notable disclosure because fluorinated natural products are exceedingly rare, and in this case it suggested that the bacterium had the capacity to mediate an enzymatic aryl fluorination reaction. However, a synthesis of the putative metabolite 1 demonstrates that the spectroscopic data are inconsistent with the proposed structure. There is no evidence that the isolated compound contained a fluorine atom.
