- Divergent Synthesis of Enantioenriched β-Functional Amines via Desymmetrization of meso-Aziridines with Isocyanides
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A highly enantioselective ring-opening desymmetrization of meso-aziridines with isocyanides was achieved in the presence of a chiral N,N′-dioxide/Mg(OTf)2 complex. The in situ generated chiral 1,4-zwitterionic intermediates were successfully trapped by intramolecular oxygen- and carbon-based nucleophiles or exogenous H2O and TMSN3, enabling a collective synthesis of various chiral vicinal amino-oxazoles, spiroindolines, β-amino amides, and tetrazole derivative in moderate to high yields with excellent enantioselectivities.
- Li, Xiangqiang,Xiong, Qian,Guan, Mingming,Dong, Shunxi,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 6096 - 6101
(2019/08/20)
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- Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles
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A silver-catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α-substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2-aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a13C-labeling experiment, according to which an unprecedented chemoselective heterodimerization of two different isocyanides generates an α-amidoketenimine intermediate, which undergoes 1,3-amino migration to form an α-imidoylketene, followed by 6 π electrocyclization.
- Hu, Zhongyan,Dong, Jinhuan,Men, Yang,Lin, Zhichen,Cai, Jinxiong,Xu, Xianxiu
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supporting information
p. 1805 - 1809
(2017/02/05)
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- Substituted Oxazole Compounds with Analgesic Activity
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Substituted oxazole derivatives corresponding to formula 1: a method for producing such compounds, pharmaceutical compositions containing such compounds, and the use of such compounds to treat pain, depression, urinary incontinence, diarrhoea, pruritus, a
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Page/Page column 11
(2009/04/24)
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- Mono alkylation of α-isocyano acetamide to its higher homologues
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Alkylation of α-isocyano acetamide (2) with alkyl halide in MeCN at 0 °C in the presence of cesium hydroxide afforded the mono-alkylated product 1 in good to excellent yield. Georg Thieme Verlag Stuttgart.
- Housseman, Christopher,Zhu, Jieping
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p. 1777 - 1779
(2008/02/04)
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- Multicomponent synthesis of epoxy-tetrahydronaphthyridine and structural diversification by subsequent fragmentation
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Three-component reaction of an α-isocyanoacetamide 7, an homoallylamine 8 and an aldehyde 9 in methanol at room temperature provides oxa-bridged tricycle 4 in good to excellent yield as a mixture of two separable diastereoisomers. In this one-pot multicom
- Fayol, Aude,Zhu, Jieping
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p. 11511 - 11519
(2007/10/03)
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- Synthesis of α-isocyano-α-alkyl(aryl)acetamides and their use in the multicomponent synthesis of 5-aminooxazole, pyrrolo[3,4-a]pyridin-5-one and 4,5,6,7-tetrahydrofuro[2,3-c]pyridine
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α-Isocyano-β-phenylpropionamide 1 is synthesized from the corresponding amino acid in excellent yield. The unique reactivity of this bifunctional compound is exploited for the development of novel multicomponent synthesis of 5-aminooxazole 6, pyrrolo[3,4-
- Fayol, Aude,Housseman, Christopher,Sun, Xiaowen,Janvier, Pierre,Bienayme, Hugues,Zhu, Jieping
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p. 161 - 165
(2007/10/03)
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- Truncated diastereoselective Passerini reaction, a rapid construction of polysubstituted oxazole and peptides having an α-hydroxy-β-amino acid component
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The reaction of aldehydes and ketones, including aliphatic and aromatic ones, with amides of α-isocyano-β-phenylpropionic acid in toluene in the presence of lithium bromide gives 2,4,5-trisubstituted oxazoles in good to excellent yield. Protected chiral α
- Cuny, Guylaine,Gámez-Monta?o, Rocio,Zhu, Jieping
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p. 4879 - 4885
(2007/10/03)
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- Antifungal Activities of &α-Isocyano-&β-phenylpropionamides
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A variety of α-isocyano-β-phenylpropionamides were synthesized and their inhibitory activities examined against Sphaerotheca fuliginea and Cladosporium fulvum.Among them, N-cyclohexyl-α-isocyano-β-phenylpropionamide (3c) was chosen as the first candidate
- Takiguchi, Kazuo,Yamada, Kunihiko,Suzuki, Mamoru,Nunami, Ken-ichi,Hayashi, Kimiaki,Matsumoto, Kazuo
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