116070-63-4Relevant academic research and scientific papers
Alkenes as Ketol Surrogates - A New Approach toward Enantiopure Acyloins
Plietker, Bernd
, p. 289 - 291 (2004)
(Matrix presented) Enantiopure α-hydroxy ketones are important building blocks in organic synthesis. This paper describes the use of cyclic ruthenates for the first catalytic regioselective oxidation of vic-diols to α-ketols. The combination of RuCl3/Oxone/NaHCO3 was used in a two-step sequence of asymmetric dihydroxylation and regioselective monooxidation for the synthesis of a broad scope of enantiopure acyloins.
Highly Enantioselective Iron-Catalyzed cis-Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-OOH Reactive Intermediate
Zang, Chao,Liu, Yungen,Xu, Zhen-Jiang,Tse, Chun-Wai,Guan, Xiangguo,Wei, Jinhu,Huang, Jie-Sheng,Che, Chi-Ming
supporting information, p. 10253 - 10257 (2016/08/24)
The development of environmentally benign catalysts for highly enantioselective asymmetric cis-dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L=N,N′-dimethyl-N,N′-bis(2-methyl-8-quinolyl)-cyclohexane-1,2-diamine) as a catalyst, cis-diols in up to 99.8 % ee with 85 % isolated yield have been achieved in AD of alkenes with H2O2as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2]+H2O2” method is applicable to both (E)-alkenes and terminal alkenes (24 examples >80 % ee, up to 1 g scale). Mechanistic studies, including18O-labeling, UV/Vis, EPR, ESI-MS analyses, and DFT calculations lend evidence for the involvement of chiral FeIII-OOH active species in enantioselective formation of the two C?O bonds.
Heterogeneous catalytic asymmetric dihydroxylation of olefins: A new polymeric support and a process improvement
Pini, Dario,Petri, Antonella,Salvadori, Piero
, p. 11321 - 11328 (2007/10/02)
A new polymeric support containing a derivative of quinine 4-chlorobenzoate and alcoholic pendent groups was found to give good enantioselectivity in many cases comparable to those obtained with the free alkaloid in homogeneous reaction conditions, providing also the known advantages of the heterogeneous process. Both aromatic and aliphatic olefins were screened, using either N-methylmorpholine-N-oxide (NMO) or potassium ferricyanide (K3Fe(CN)6) as secondary oxidants.
Preclusion of the "second cycle" in the osmium-catalyzed asymmetric dihydroxylation of olefins leads to a superior process
Kwong, Hoi-Lun,Sorato, Carla,Ogino, Yasukazu,Chen, Hou,Sharpless, K. Barry
, p. 2999 - 3002 (2007/10/02)
The highest enantioselectivities yet obtained in catalytic asymmetric dihydroxylations are realized using potassium hexacyanoferrate(III) [potassium ferricyanide, K3Fe(CN)6] as the reoxidant.
