33535-80-7Relevant academic research and scientific papers
Chiral (cyclopentadienone)iron complexes with a stereogenic plane as pre-catalysts for the asymmetric hydrogenation of polar double bonds
Bai, Xishan,Cettolin, Mattia,Mazzoccanti, Giulia,Pierini, Marco,Piarulli, Umberto,Colombo, Valentina,Dal Corso, Alberto,Pignataro, Luca,Gennari, Cesare
supporting information, p. 1415 - 1424 (2019/02/09)
In this paper, we describe a small library of easy-to-prepare chiral (cyclopentadienone)iron pre-catalysts for enantioselective C[dbnd]O and C[dbnd]N hydrogenations. Starting from readily accessible achiral materials, six chiral (cyclopentadienone)iron complexes (1a-f) possessing a stereogenic plane were synthesized in racemic form. Based on the screening of pre-catalysts (±)-1a-f in the hydrogenation of ketones and ketimines, we selected two complexes (1a and 1d) for resolution by semipreparative enantioselective HPLC. The absolute configuration of the separated enantiomers of 1a and 1d was assigned by XRD analysis (1a) and by comparison between experimental and DFT-calculated ECD and ORD spectra (1d). The enantiopure pre-catalysts (S)-1a and (R)-1d were tested in the asymmetric hydrogenation of several ketones and ketimines and showed good activity and modest enantioselectivity, the e.e. values ranging from very low to moderate (54%).
Synthesis of Planar Chiral Shvo Catalysts for Asymmetric Transfer Hydrogenation
Dou, Xiaowei,Hayashi, Tamio
supporting information, p. 1054 - 1058 (2016/04/19)
A new type of planar chiral Shvo catalysts, where the chirality is based solely on different substitution flanking the C£O function, was prepared and used for transfer hydrogenation of imines and ketones. The reduction of ketimines represented by N-(1-phe
A metal-free cycloaddition approach to highly substituted aromatic boronic esters
Moore, Jane E.,York, Mark,Harrity, Joseph P. A.
, p. 860 - 862 (2007/10/03)
Alkynylboronates participate in [4+2] benzannulation reactions to furnish highly functionalised aromatic boronic esters, further manipulation of these boronic esters has been achieved via oxidation and Suzuki coupling reactions.
Diastereoselective synthesis of C-glycosylnorbornenones
Del Valle, Jose L.,Torroba, Tomas,Marcaccini, Stefane,Paoli, Paola,Williams, David J.
, p. 8259 - 8278 (2007/10/02)
Thermal reaction of (E)-3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-C-nitro-D-galacto- (1a) and D-manno-hept-1-enitol (1b) with 2-methyl-3,4-diaryl-5-phenylcyclopentadienones (2a-c) afforded diastereoselectively 1-methyl-2,3-diaryl-4-phenyl-(5S,6R)-5-exo-(D-galacto- (3a-c) and -(5R,6S)-5-exo-(D-manno-penta-O-acetylpentitol-1-yl)-6-endo-nitrobicyc lo[2.2.1]hept-2-en-7-ones (6a-c) and variable amounts of the 1-phenyl-4-methyl regioisomers 4a-c and 7a-c, depending upon the p-substituent in the aryl moiety. 1-C-arylalditols 5, 8-9 are also obtained in refluxing xylene.
