Abstract
By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from 1H NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.
| Original language | English |
|---|---|
| Pages (from-to) | 1535-1540 |
| Number of pages | 6 |
| Journal | Tetrahedron: Asymmetry |
| Volume | 5 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 1994 |
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ASJC Scopus subject areas
- Inorganic Chemistry
- Organic Chemistry
- Materials Chemistry
- Drug Discovery
Cite this
Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one. / Cardillo, Barbara; Galeazzi, Roberta; Mobbili, Giovanna; Orena, Mario; Rossetti, Monica.
In: Tetrahedron: Asymmetry, Vol. 5, No. 8, 1994, p. 1535-1540.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Diastereoselective hetero-diels-alder cycloaddition of a C-nitroso compound prepared starting from a homochiral imidazolidin-2-one
AU - Cardillo, Barbara
AU - Galeazzi, Roberta
AU - Mobbili, Giovanna
AU - Orena, Mario
AU - Rossetti, Monica
PY - 1994
Y1 - 1994
N2 - By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from 1H NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.
AB - By Swern oxidation of the hydroxamic acid 3, prepared from the homochiral imidazolidin-2-one 1, the transient C-nitroso derivative 4 is obtained, and its cycloaddition to either cyclohexadiene or cyclopentadiene proceeds with high diastereoselection, owing to the conformational stability of 4. The stereochemical outcome of the reaction is determined from 1H NMR data and further confirmed by the specific rotation value of 7, obtained by cleavage of the major cycloadduct 5a.
UR - http://www.scopus.com/inward/record.url?scp=0028086466&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0028086466&partnerID=8YFLogxK
U2 - 10.1016/0957-4166(94)80123-1
DO - 10.1016/0957-4166(94)80123-1
M3 - Article
AN - SCOPUS:0028086466
VL - 5
SP - 1535
EP - 1540
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 8
ER -