Synthesis of both enantiomers of ferrocene[1,2-c]1H-quinolin-2-one by diastereoselective deproto-zincation of sugar-derived ferrocene esters
Synthesis of both enantiomers of ferrocene[1,2-c]1H-quinolin-2-one by diastereoselective deproto-zincation of sugar-derived ferrocene esters
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通过糖衍生二茂铁酯的非对映选择性脱原锌化合成二茂铁[1,2-c]1H-喹啉-2-酮的两种对映体
DOI：
10.1039/c2ra21045b
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发表时间：
2012
期刊：
影响因子：
--
通讯作者：
Aare Sreeshailam
中科院分区：
文献类型：
--
作者：
Ushiro;Y.;Hasegawa;Y.;Nahatame;S.;Shimizu;H.;Takaki;S.;Hamada;A.;Nakagawa;C.;Aare Sreeshailam
研究了使用锂锌碱对几种糖衍生的二茂铁酯进行非对映选择性脱原金属化。双[(R)-1-苯乙基]氨基作为配体在碘化后得到91% de的双丙酮-D-葡萄糖基(SP)-2-碘二茂铁酯，而RP是使用2,2,6,6-四甲基哌啶子基作为配体从α-D-呋喃葡萄糖合成的。 (RP)-和(SP)-二茂铁[1,2-c]1H-喹啉-2-酮均通过随后的环化偶联得到，尽管注意到它们的外消旋化。
The diastereoselective deproto-metallation of several sugar-derived ferrocene esters using lithium-zinc bases was studied. While bis[(R)-1-phenylethyl]amino as the ligand afforded the diacetone-D-glucose-based (SP)-2-iodoferrocene ester in 91% de after iodination, the RP was synthesized from α-D-glucofuranose using 2,2,6,6-tetramethylpiperidino as the ligand. Both (RP)- and (SP)-ferrocene[1,2-c]1H-quinolin-2-one were reached by subsequent cyclizing couplings, albeit their racemization was noted.