Abstract
Helical chiral 2-aminopyridinium ions were designed as a significantly more acidic (active) dual hydrogen-bonding catalyst than commonly used (thio)urea-based systems. The helicene framework was specifically utilized to position an inherently chiral barrier on the hydrogen-bonding side of the catalyst. The catalyst reactivity and enantioselectivity were successfully demonstrated in additions of 4,7-dihydroindoles to nitroalkenes (0.5-2 mol % catalyst loadings, up to 98:2 er).
| Original language | English |
|---|---|
| Pages (from-to) | 4536-4537 |
| Number of pages | 2 |
| Journal | Journal of the American Chemical Society |
| Volume | 132 |
| Issue number | 13 |
| DOIs | |
| State | Published - Apr 7 2010 |
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ASJC Scopus subject areas
- Chemistry(all)
- Catalysis
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Helical chiral 2-aminopyridinium ions : A new class of hydrogen bond donor catalysts. / Takenaka, Norito; Chen, Jinshui; Captain, Burjor; Sarangthem, Robindro Singh; Chandrakumar, Appayee.
In: Journal of the American Chemical Society, Vol. 132, No. 13, 07.04.2010, p. 4536-4537.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Helical chiral 2-aminopyridinium ions
T2 - A new class of hydrogen bond donor catalysts
AU - Takenaka, Norito
AU - Chen, Jinshui
AU - Captain, Burjor
AU - Sarangthem, Robindro Singh
AU - Chandrakumar, Appayee
PY - 2010/4/7
Y1 - 2010/4/7
N2 - Helical chiral 2-aminopyridinium ions were designed as a significantly more acidic (active) dual hydrogen-bonding catalyst than commonly used (thio)urea-based systems. The helicene framework was specifically utilized to position an inherently chiral barrier on the hydrogen-bonding side of the catalyst. The catalyst reactivity and enantioselectivity were successfully demonstrated in additions of 4,7-dihydroindoles to nitroalkenes (0.5-2 mol % catalyst loadings, up to 98:2 er).
AB - Helical chiral 2-aminopyridinium ions were designed as a significantly more acidic (active) dual hydrogen-bonding catalyst than commonly used (thio)urea-based systems. The helicene framework was specifically utilized to position an inherently chiral barrier on the hydrogen-bonding side of the catalyst. The catalyst reactivity and enantioselectivity were successfully demonstrated in additions of 4,7-dihydroindoles to nitroalkenes (0.5-2 mol % catalyst loadings, up to 98:2 er).
UR - http://www.scopus.com/inward/record.url?scp=77950801125&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77950801125&partnerID=8YFLogxK
U2 - 10.1021/ja100539c
DO - 10.1021/ja100539c
M3 - Article
C2 - 20232867
AN - SCOPUS:77950801125
VL - 132
SP - 4536
EP - 4537
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 13
ER -