525585-56-2Relevant academic research and scientific papers
Chiral relay in NHC-mediated asymmetric β-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine
Duguet, Nicolas,Donaldson, Adele,Leckie, Stuart M.,Douglas, James,Shapland, Peter,Brown, Thomas B.,Churchill, Gwydion,Slawin, Alexandra M.Z.,Smith, Andrew D.
experimental part, p. 582 - 600 (2010/08/19)
The synthesis of a range of C2-symmetric imidazolinium salts from (1R,2R)-cyclohexane-1,2-diamine, and an evaluation of the reactivity and asymmetric induction of the derived NHCs as catalysts for the asymmetric synthesis of β-lactams, is reported. In this series, optimal enantioselectivity (up to 70% ee) is observed using N-benzyl or N-1-naphthylmethyl-substituted NHCs, consistent with a chiral relay effect operating to dictate the stereochemical outcome of this reaction.
Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model
Zhang, Wei,Basak, Arindrajit,Kosugi, Yuji,Hoshino, Yujiro,Yamamoto, Hisashi
, p. 4389 - 4391 (2007/10/03)
(Chemical Equation Presented) Bishydroxamic acid derivatives are used as ligands for a vanadium catalyst in the preparation of epoxy alcohols (see scheme). The methodology uses aqueous tert-butyl hydroperoxide (TBHP) as an achiral oxidant, low catalyst loading, low reaction temperatures (0°C to room temperature), and simple workup procedures. The reaction is applied to the kinetic resolution of a secondary allylic alcohol and the preparation of small epoxy alcohols. R1, R2, R3: alkyl, aryl, H.
One catalyst for two distinct reactions: Sequential asymmetric hetero Diels-Alder reaction and diethylzinc addition
Du, Haifeng,Zhang, Xue,Wang, Zheng,Ding, Kuiling
, p. 9465 - 9477 (2007/10/03)
This paper describes the successful development of a series of chiral zinc catalysts containing (R)-3,3′-Br2-BINOL ligand and various diimine activators for enantioselective HDA reaction of Danishefsky's diene with aldehydes through a combinato
Catalytic asymmetric epoxidation
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Page/Page column 8; 19, (2010/02/12)
The present invention relates to the synthesis of chiral epoxides via a catalytic asymmetric oxidation of olefins. Additionally, the methodology provides a method of asymmetrically oxidizing sulfides and phosphines. This asymmetric oxidation employs a catalyst system composed of a metal and a chiral bishydroxamic acid ligand, which, in the presence of a stoichiometric oxidation reagent, serves to asymmetrically oxidize a variety of substrates.
An easy and clean synthesis of chiral 3,4-diaryl-2,5-diazabicyclo[4.4.0]decanes by reductive intramolecular coupling of chiral diimines
Hesemann, Peter,Moreau, Joel J. E.,Soto, Thierry
, p. 183 - 189 (2007/10/03)
A clean and efficient reductive intramolecular coupling of diimines prepared from (1R,2R)-cyclohexanediamine gave chiral 2,3-diarylpiperazines.
