ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The Michael addition of 2-substituted cyclopentanones 1 to β-nitrostyrene 2 proceeds at room temperature in the presence of catalysts such as NEt3, 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 1H-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, rac-4a was established from X-ray crystallography.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19953370105
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