- Fluorocyclization of Vinyl Azides for the Formation of 3-Azido Heterocycles
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3-Azido saturated heterocycles are important for therapeutic-development but challenging to prepare. Disclosed herein is a novel synthetic strategy for 3-azido heterocycles via fluorocyclization of the easily available vinyl azides. This transfor-mation proceeded under mild conditions and provided a wide range of 3-azido heterocycles in good to excellent yields. Notably, the azido group plays an indispensable role to promote rapid and regioselective fluorocyclization. Moreover, the protocol was highlighted by gram-scale synthesis and further synthetic transformations.
- Bai, Diangang,Li, Linxuan,Li, Xiaomeng,Lu, Ying,Ning, Yongquan,Rajendra Prasad Redd, Bhoomireddy,Wu, Yong
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- Silver-free activation of ligated gold(I) chlorides: The use of [Me3NB12Cl11]- as a weakly coordinating anion in homogeneous gold catalysis
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Phosphane and N-heterocyclic carbene ligated gold(I) chlorides can be effectively activated by Na[Me3NB12Cl11] (1) under silver-free conditions. This activation method with a weakly coordinating closo-dodecaborate anion was shown to be suitable for a large variety of reactions known to be catalyzed by homogeneous gold species, ranging from carbocyclizations to heterocyclizations. Additionally, the capability of 1 in a previously unknown conversion of 5-silyloxy-1,6-allenynes was demonstrated.
- Wegener, Michael,Huber, Florian,Bolli, Christoph,Jenne, Carsten,Kirsch, Stefan F.
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supporting information
p. 1328 - 1336
(2015/02/05)
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- Gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides: A reliable access to enantioenriched pyrrolidin-3-ones
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A gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides has been developed, which provides a reliable access to synthetically useful chiral pyrrolidin-3-ones with excellent ee, by combining the chiral tert-butylsulfinimine chemistry and gold catalysis. This methodology has also been used in the facile synthesis of natural product (-)-irniine. The use of readily available starting materials, a broad substrate scope, a simple procedure and the mild nature of this reaction render it a viable alternative for the synthesis of enantioenriched pyrrolidin-3-ones.
- Shu, Chao,Li, Long,Yu, Yong-Fei,Jiang, Shuang,Ye, Long-Wu
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supporting information
p. 2522 - 2525
(2014/03/21)
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- Gold-catalyzed synthesis of 3-pyrrolidinones and nitrones from N-sulfonyl hydroxylamines via oxygen-transfer redox and 1,3-sulfonyl migration
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Golden touch: Gold-catalyzed reaction of N-sulfonyl hydroxylamines with terminal alkyne led to 3-pyrrolidinones by means of an oygen-transfer redox reaction. This protocol constitutes a direct method for forming α-amino carbonyl compounds. In sharp contrast, those with internal alkynes underwent 1,3-sulfonyl migration leading to 3-sulfonyl cyclic nitrones.
- Yeom, Hyun-Suk,So, Eunsu,Shin, Seunghoon
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p. 1764 - 1767
(2011/04/16)
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- Intramolecular N-H insertion of α-diazocarbonyls catalyzed by Cu(acac)2: An efficient route to derivatives of 3-oxoazetidines, 3-oxopyrrolidines and 3-oxopiperidines
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Cu(acac)2 was found to be an efficient catalyst for the intramolecular N-H insertion by carbenoids. The competitive intramolecular C-H insertion by carbenoids is not a problem in the diazo decomposition reaction with Cu(acac)2 as catalyst. The reaction provided derivatives of 3-oxoazetidine, 3-oxopyrrolidine and 3-oxopiperidine in moderate to good yields.
- Wang, Jianbo,Hou, Yihua,Wu, Peng
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p. 2277 - 2280
(2007/10/03)
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- SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 1-CYCLOPROPYL-6,8-DIFLUORO-7-(2-SUBSTITUTED 4,6-DIHYDRO-1H-PYRROLOTHIAZOL-5-YL)-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID
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Quinolone derivatives (9 and 10) substituted with bicyclothiazole (7) and (8) at C-7 position were synthesized.Bicyclothiazole derivatives (7 and 8) were prepared through 9 steps by way of the 4-bromo-3-oxopyrrolidine (16) was a key intermediate and intro
- Kim, Wan-Joo,Kim, Bong-Jin,Lee, Tae-Suk,Nam, Keun-Soo,Kim, Keun-Jae
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p. 1389 - 1398
(2007/10/02)
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- PREPARATION OF 1-TOSYL-2- AND 3-PYRROLIDINONES 'VIA' KETENES AND CARBENES
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Catalytic decomposition of 1-diazo-4-tosylamino-2-butanone 1a, -2-pentanone 1b, and -2-hexanone 1c, results in the quantitative formation of the 1-tosyl-3-pyrrolidinones 2a, 2b and 2c, while the photolysis afforded the rearranged esters, 3a, 3b and 3c, or
- Saba, Antonio,Selva, Antonio
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p. 867 - 870
(2007/10/02)
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