911061-50-2Relevant articles and documents
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.
Synthesis and conformational analysis of α,β-difluoro-γ- amino acid derivatives
Hunter, Luke,Jolliffe, Katrina A.,Jordan, Meredith J. T.,Jensen, Paul,MacQuart, Rene B.
supporting information; experimental part, p. 2340 - 2343 (2011/04/22)
Conformationally restricted amino acids are of interest because they can be incorporated into shape-controlled peptides for applications in biotechnology and medicine.Within this context, β-and γ-amino acids have attracted considerable attention since their homologated carbon backbones are amenable to functionalization in ways that are not achievable with a-amino acids. For example, Seebach et al. have shown that the different diastereoisomers of α-fluoroβ-alanine lead to differently folded structures when they are incorporated into b-heptapeptides. These conformational differences are attributed to the preference of C-F bonds to align antiparallel to adjacent amide C=O bonds and gauche to vicinal C-N bonds. This result is a notable example of a growing body of research demonstrating that the C-F bond can be exploited as a conformational tool to optimize the properties of diverse functional molecules including pharmaceuticals, organocatalysts and liquid crystals.
Enantioselective synthesis of (+)-(S,S)-reboxetine
Siddiqui, Shafi A.,Narkhede, Umesh C.,Lahoti, Rajgopal J.,Srinivasan, Kumar V.
, p. 1771 - 1773 (2008/02/04)
An efficient enantioselective synthesis leading directly to (+)-(S,S)-reboxetine has been described from commercially available trans-cinnammyl bromide using Sharpless asymmetric dihydroxylation as the key step. Georg Thieme Verlag Stuttgart.
