85288-37-5Relevant articles and documents
Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation
Chang, Sukbok,Jung, Hoimin,Keum, Hyeyun,Kweon, Jeonguk
supporting information, p. 5811 - 5818 (2020/04/10)
Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.
Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions
Chang, Sukbok,Jung, Hoimin,Kim, Dongwook,Lee, Jeonghyo,Lee, Jia,Park, Juhyeon
, p. 12324 - 12332 (2020/08/06)
Herein, we report the development of a tailored cobalt catalyst system of Cp*Co(III)(LX) toward intramolecular C-H nitrene insertion of azidoformates to afford cyclic carbamates. The cobalt complexes were easy to prepare and bench-stable, thus offering a convenient reaction protocol. The catalytic reactivity was significantly improved by the electronic tuning of the bidentate LX ligands, and the observed regioselectivity was rationalized by the conformational analysis and DFT calculations of the transition states. The superior performance of the newly developed cobalt catalyst system could be broadly applied to both C(sp2)-H and C(sp3)-H carbamation reactions under mild conditions.
Synthesis of Chiral 5-Aryl-2-oxazolidinones via Halohydrin Dehalogenase-Catalyzed Enantio- and Regioselective Ring-Opening of Styrene Oxides
Wan, Nanwei,Zhou, Xiaoying,Ma, Ran,Tian, Jiawei,Wang, Huihui,Cui, Baodong,Han, Wenyong,Chen, Yongzheng
supporting information, p. 1201 - 1207 (2020/02/05)
An efficient biocatalytic approach for enantio- and regioselective ring-opening of styrene oxides with cyanate was developed by using the halohydrin dehalogenase HheC from Agrobacterium radiobacter AD1, generating the corresponding chiral 5-aryl-2-oxazoli
Regioselective Ring-Opening of Styrene Oxide Derivatives Using Halohydrin Dehalogenase for Synthesis of 4-Aryloxazolidinones
Wan, Nanwei,Tian, Jiawei,Zhou, Xiaoying,Wang, Huihui,Cui, Baodong,Han, Wenyong,Chen, Yongzheng
, p. 4651 - 4655 (2019/08/27)
A biocatalytic approach towards a range of 4-aryloxazolidinones is developed using a halohydrin dehalogenase from Ilumatobacter coccineus (HheG) as biocatalyst. The method is based on the HheG-catalyzed α-position regioselective ring-opening of styrene oxide derivatives with cyanate as a nucleophile, producing the corresponding 4-aryloxazolidinones in moderate to good yields. Synthesis of enantiopure 4-aryloxazolidinones is also achievable using chiral epoxide materials. (Figure presented.).
Method of biocatalytically synthesizing 4-substituted oxazolidinone compound
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Paragraph 0050; 0051; 0052; 0053, (2019/04/27)
The invention discloses a biocatalytic technology of synthesizing a 4-substituted oxazolidinone compound by carrying out a reaction on a halohydrin dehalogenase catalyzed epoxy compound and cyanate. The reaction takes the epoxy compound as a primer, cyanate as a nucleophilic ring opening reagent and halohydrin dehalogenase which is originated from an Ilumatobacter coccineus strain and has high alpha-offensive ring opening area selectivity as a biocatalyst. The reaction is carried out in a water phase and is mild in reaction condition. The invention is the biocatalytic method of catalyzing theepoxy compound to synthesize the 4-substituted oxazolidinone compound by using the halohydrin dehalogenase for the first time. The method has a wide application prospect in design of an oxazolidinonedrug and green manufacturing aspect thereof.
Aluminium-Catalysed Oxazolidinone Synthesis and their Conversion into Functional Non-Symmetrical Ureas
Laserna, Victor,Guo, Wusheng,Kleij, Arjan W.
, p. 2849 - 2854 (2015/09/28)
An efficient and practical aluminium-catalysed approach towards a range of functional oxazolidinones is reported. The method is based on cheap and readily available starting materials including terminal and internal (bicyclic) epoxides and phenyl carbamate. The oxazolidinones serve as highly useful synthons for the high yield preparation of non-symmetrical ureas by nucleophilic ring-opening affording the targeted urea compounds with excellent functional group diversity, high regioselectivity and isolated yields up to >99%.
THE INTRAMOLECULAR CHEMISTRY OF BENZYL AND PHENETHYL AZIDOFORMATES
Meth-Cohn, Otto,Patel, Dalpat,Rhouati, Salah
, p. 5085 - 5088 (2007/10/02)
Benzyl azidoformates yield one of a variety of products on spray pyrolysis dependent upon substitution, including oxazoloazepines, their syn or anti dimers, their dimers, a benzoxazinone or aryl isocyanate; the phenethyl analogues give stable oxazinoazepines.
