Abstract
A number of trans-3-acetyl-4-alkylpyrrolidin-2-ones 8a-d and 11a,b were prepared and reduction of the keto group, carried out with KBH4 in CH3OH, led mainly to 3-hydroxyethylpyrrolidin-2-ones 13a-d and 19a,b with high stereoselection. Configuration of the newly formed stereogenic centre on the hydroxyethyl chain was assigned by 1H NMR data supported by molecular mechanic calculations and eventually confirmed by X-ray diffraction analysis of p-iodobenzoate derivative 15.
| Original language | English |
|---|---|
| Pages (from-to) | 587-605 |
| Number of pages | 19 |
| Journal | Tetrahedron: Asymmetry |
| Volume | 10 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - Feb 16 1999 |
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ASJC Scopus subject areas
- Inorganic Chemistry
- Organic Chemistry
- Materials Chemistry
- Drug Discovery
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Stereoselective reduction of chiral trans-3-acetyl 4-alkylpyrrolidin-2- ones. / Galeazzi, Roberta; Geremia, Silvano; Mobbili, Giovanna; Orena, Mario.
In: Tetrahedron: Asymmetry, Vol. 10, No. 3, 16.02.1999, p. 587-605.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereoselective reduction of chiral trans-3-acetyl 4-alkylpyrrolidin-2- ones
AU - Galeazzi, Roberta
AU - Geremia, Silvano
AU - Mobbili, Giovanna
AU - Orena, Mario
PY - 1999/2/16
Y1 - 1999/2/16
N2 - A number of trans-3-acetyl-4-alkylpyrrolidin-2-ones 8a-d and 11a,b were prepared and reduction of the keto group, carried out with KBH4 in CH3OH, led mainly to 3-hydroxyethylpyrrolidin-2-ones 13a-d and 19a,b with high stereoselection. Configuration of the newly formed stereogenic centre on the hydroxyethyl chain was assigned by 1H NMR data supported by molecular mechanic calculations and eventually confirmed by X-ray diffraction analysis of p-iodobenzoate derivative 15.
AB - A number of trans-3-acetyl-4-alkylpyrrolidin-2-ones 8a-d and 11a,b were prepared and reduction of the keto group, carried out with KBH4 in CH3OH, led mainly to 3-hydroxyethylpyrrolidin-2-ones 13a-d and 19a,b with high stereoselection. Configuration of the newly formed stereogenic centre on the hydroxyethyl chain was assigned by 1H NMR data supported by molecular mechanic calculations and eventually confirmed by X-ray diffraction analysis of p-iodobenzoate derivative 15.
UR - http://www.scopus.com/inward/record.url?scp=0033548155&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033548155&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(99)00031-2
DO - 10.1016/S0957-4166(99)00031-2
M3 - Article
AN - SCOPUS:0033548155
VL - 10
SP - 587
EP - 605
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 3
ER -