- Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids
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Electrophilic aminations involve an umpolung of a nitrogen atom, providing an alternate, distinctive synthetic strategy. The recent advent of various designed O-substituted hydroxylamines has significantly advanced this research field. An underappreciated
- Yu, Jin-Sheng,Espinosa, Miguel,Noda, Hidetoshi,Shibasaki, Masakatsu
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supporting information
p. 10530 - 10537
(2019/07/03)
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- Enzymatic resolution of 2-substituted tetrahydroquinolines. Convenient approaches to tricyclic quinoxalinediones as potent NMDA-glycine antagonists
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Two approaches leading to the enantiomerically pure tricyclic quinoxalinedione class of NMDA-glycine antagonists using enzymatic resolutions are described. An intermediate, racemic methyl 1,2,3,4- tetrahydroquinoline-2-carboxylate 3, was resolved to (S)-3
- Katayama, Seiji,Ae, Nobuyuki,Nagata, Ryu
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p. 4295 - 4299
(2007/10/03)
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- Benzocarbacephems from quinolines
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The azetidinones 1,2 and 3 have been prepared from simple quinoline derivatives. 2,2a,3,4-Tetrahydro-1H-azeto[1,2-a]quinolin-1-one 1 has been synthesised from quinoline N-oxide and, more efficiently, in three steps from 2-methylquinoline. In both routes 1,2,3,4-tetrahydroquinoline-2-acetic acid 7 is prepared as an intermediate and this is then cyclised to the azetidinone 1. The 8-hydroxyazetidinone 3 has been synthesised by analogous routes, the hydroxy group being protected as an isopropyl ether during the intermediate steps. An X-ray crystal structure of compound 3 has been obtained and this reveals intramolecular hydrogen bonding between the hydroxy and carbonyl groups. The unsaturated azetidinone 2 has been prepared from 1 by stereoselective radical bromination at C-4 followed by dehydrobromination with DBU.
- Gilchrist, Thomas L.,Rahman, Adrian
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p. 1203 - 1207
(2007/10/03)
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