Highly diastereoselective conjugate addition of aryllithium to chiral β-nitrostyrene derivative : An application to the asymmetric synthesis of 4 -aryl -1,2,3,4 -tetrahydroisoquinoline

Highly diastereoselective conjugate addition of aryllithium to chiral β-nitrostyrene derivative : An application to the asymmetric synthesis of 4 -aryl -1,2,3,4 -tetrahydroisoquinoline
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DOI:
10.1246/cl.2007.64
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发表时间:
2007-01
期刊:
影响因子:
1.6
通讯作者:
M. Asami;Ayako Taketoshi;K. Miyoshi;Hayato Hoshino;K. Sakakibara
M. Asami;Ayako Taketoshi;K. Miyoshi;Hayato Hoshino;K. Sakakibara
中科院分区:
化学4区
文献类型:
--
作者:
M. Asami;Ayako Taketoshi;K. Miyoshi;Hayato Hoshino;K. Sakakibara

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以(S,S)-1,2-二(l-羟丙基)苯为手性缩醛,实现了芳基锂与β-硝基苯乙烯衍生物的高度非对映选择性共轭加成。加合物以高对映体过量(ee)转化为4-芳基-1,2,3,4-四氢异喹啉。
Highly diastereoselective conjugate addition of aryllithium to β-nitrostyrene derivative, having chiral acetal moiety derived from (S,S)-1,2-bis(l-hydroxypropyl)benzene, was achieved. The adduct was transformed to 4-aryl-1,2,3,4-tetrahydroisoquinoline in high enantiomeric excess (ee).