Abstract
The alkylation of dienolates generated from 3-methoxycycloalk-2-enones having a 3′-hydroxyl alkenyl chain provides the corresponding quaternized cycloalkenones in a highly diastereoselective manner. The high degree of stereocontrol in the α-quaternization possibly implies intervention of a rigid chelating transition state that allows an efficient 1,4-asymmetric induction to take place.
| Original language | English |
|---|---|
| Pages (from-to) | 1202-1207 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 77 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - Jan 20 2012 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Stereoselective α-quaternization of 3-methoxycycloalk-2-enones via 1,4-diastereoinduction of alkoxy dienolates. / Moustafa, Gamal A I; Kamada, Yasumasa; Tanaka, Tetsuaki; Yoshimitsu, Takehiko.
In: Journal of Organic Chemistry, Vol. 77, No. 2, 20.01.2012, p. 1202-1207.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Stereoselective α-quaternization of 3-methoxycycloalk-2-enones via 1,4-diastereoinduction of alkoxy dienolates
AU - Moustafa, Gamal A I
AU - Kamada, Yasumasa
AU - Tanaka, Tetsuaki
AU - Yoshimitsu, Takehiko
PY - 2012/1/20
Y1 - 2012/1/20
N2 - The alkylation of dienolates generated from 3-methoxycycloalk-2-enones having a 3′-hydroxyl alkenyl chain provides the corresponding quaternized cycloalkenones in a highly diastereoselective manner. The high degree of stereocontrol in the α-quaternization possibly implies intervention of a rigid chelating transition state that allows an efficient 1,4-asymmetric induction to take place.
AB - The alkylation of dienolates generated from 3-methoxycycloalk-2-enones having a 3′-hydroxyl alkenyl chain provides the corresponding quaternized cycloalkenones in a highly diastereoselective manner. The high degree of stereocontrol in the α-quaternization possibly implies intervention of a rigid chelating transition state that allows an efficient 1,4-asymmetric induction to take place.
UR - http://www.scopus.com/inward/record.url?scp=84862973846&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84862973846&partnerID=8YFLogxK
U2 - 10.1021/jo2022789
DO - 10.1021/jo2022789
M3 - Article
C2 - 22208771
AN - SCOPUS:84862973846
VL - 77
SP - 1202
EP - 1207
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 2
ER -