Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade.

Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade.
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DOI:
10.1021/ja2119833
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发表时间:
2012-03-07
影响因子:
15
通讯作者:
Ellman, Jonathan A.
Ellman, Jonathan A.
中科院分区:
化学1区
文献类型:
--
作者:
Duttwyler, Simon;Lu, Colin;Rheingold, Arnold L.;Bergman, Robert G.;Ellman, Jonathan A.

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发展了一种多用途的级联反应,得到高度取代的1,2,3,6-四氢吡啶。它包括铑(I)催化的C-H活化-炔偶联,然后电环化和随后的酸/硼氢化物促进的还原。该一锅法得到目标化合物,产率高达95%,非对映体纯度>95%。
A versatile reaction cascade leading to highly substituted 1,2,3,6-tetrahydropyridines has been developed. It comprises rhodium(I)-catalyzed C–H activation–alkyne coupling followed by electrocyclization and subsequent acid/borohydride-promoted reduction. This one pot procedure affords the target compounds in up to 95% yields and with >95% diastereomeric purity.
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