One-pot enantioselective construction of indoloquinolizidine derivatives bearing five contiguous stereocenters using aliphatic aldehydes, nitroethylenes, and tryptamine.
One-pot enantioselective construction of indoloquinolizidine derivatives bearing five contiguous stereocenters using aliphatic aldehydes, nitroethylenes, and tryptamine.
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DOI：
10.1039/c4cc01929f
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发表时间：
2014-08
影响因子：
4.9
通讯作者：
Yun-Xuan Tan;Han-Lin Luan;Hua-Chen Lin;Xingwen Sun;Xiao‐Di Yang;Han-Qing Dong;G. Lin
中科院分区：
文献类型：
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作者：
Yun-Xuan Tan;Han-Lin Luan;Hua-Chen Lin;Xingwen Sun;Xiao‐Di Yang;Han-Qing Dong;G. Lin
建立了一个有机催化级联反应的建设吲哚喹嗪衍生物轴承5个连续的立体中心，从容易获得的脂肪醛，硝基乙烯，色胺。这种一锅法给出了30-55%的总产率和优异的d.r.（在所有情况下>20：1）和ee（91-98%）。此外，通过NBS介导的环化反应，制备了含四元立体碳中心的吲哚并喹嗪。
An organocatalytic cascade reaction was established for the construction of indoloquinolizidine derivatives bearing five contiguous stereocenters from readily available aliphatic aldehydes, nitroethylenes, and tryptamine. This one-pot process gave 30-55% overall yields with excellent d.r. (>20 : 1 in all cases) and ee (91-98%). Additionally, quaternary stereogenic carbon center-containing indoloquinolizidines were prepared through NBS-mediated cyclization of one of the intermediates.