STUDIES ON DIASTEREOSELECTIVE ADDITIONS OF 2-SUBSTITUTED CYCLOPENTANONES TO BETA-NITROSTYRENE
STUDIES ON DIASTEREOSELECTIVE ADDITIONS OF 2-SUBSTITUTED CYCLOPENTANONES TO BETA-NITROSTYRENE
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DOI：
10.1002/prac.19953370105
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发表时间：
1995-01-01
期刊：
影响因子：
--
通讯作者：
RAMM, M
中科院分区：
文献类型：
--
作者：
DEUTSCH, J;NICLAS, HJ;RAMM, M
The Michael addition of 2-substituted cyclopentanones 1 to beta-nitrostyrene 2 proceeds at room temperature in the presence of catalysts such as NEt(3), DMAP, KOAc, or Ni(acac)(2) leading to 2-substituted 2-(2-nitro-1-phenylethyl)cyclopentanones 3/4. Depending on substituents R in 1 compounds rac-3/4 may be obtained with high diastereoselectivity. The influences of reaction conditions were studied and the diastereomeric ratio was determined by means of H-1-NMR spectroscopy. In the cases of rac-3/4a-c, rac-3g-i, rac-3k, the diastereomers could be isolated in pure form. The configuration of compounds rac-3a and rac-4a was established from X-ray crystallography.
