Enantioselective synthesis of (S)-3-hydroxy-3-phenyl-3,4-dihydroquinolin-2(1H)-one ring system
Enantioselective synthesis of (S)-3-hydroxy-3-phenyl-3,4-dihydroquinolin-2(1H)-one ring system
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DOI：
10.1055/s-2006-958928
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发表时间：
2007-01-04
影响因子：
2.6
通讯作者：
Pedro, Jose R.
中科院分区：
文献类型：
--
作者：
Blay, Gonzalo;Cardona, Luz;Pedro, Jose R.
以（2S，5S）-顺式-2-叔丁基-5-苯基-1，3，4-二氢喹啉-2（1H）-酮为原料，3-二氧戊环-4-酮与取代的邻-硝基苄基溴，然后将硝基还原为胺，伴随着二氧戊环酮环的分子内氨解。
A series of new enantiomerically pure (S)-3-hydroxy-3-phenyl-3,4-dihydroquinolin-2(1H)-ones was prepared in good yields according to a two-step synthesis using a benzylation of the sodium enolate of the (2S,5S)-cis-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one with substituted o-nitrobenzyl bromides followed by reduction of the nitro group to amine with concomitant intramolecular aminolysis of the dioxolanone ring.