Abstract
A new asymmetric protocol for the synthesis of chiral tetrahydroquinolines from 2-aminochalcones via a two-step one-pot consecutive process (cyclization/asymmetric reduction) has been developed using chiral phosphoric acid as the sole catalyst. 2-Aminochalcones were converted into the corresponding quinolines through chiral phosphoric acid-catalyzed dehydrative cyclization, and the resultant quinolines were subsequently reduced to the chiral tetrahydroquinolines via chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester. Various 2-aminochalcones could be applicable to this protocol, and the desired tetrahydroquinolines were obtained in excellent yields and with excellent enantioselectivities. Furthermore, the utility of this protocol has been successfully demonstrated in the highly efficient synthesis of estrogen receptor modulator.
| Original language | English |
|---|---|
| Pages (from-to) | 12486-12495 |
| Number of pages | 10 |
| Journal | Journal of Organic Chemistry |
| Volume | 83 |
| Issue number | 20 |
| DOIs | |
| Publication status | Published - 2018 Oct 19 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Enantioselective Synthesis of Tetrahydroquinolines from 2-Aminochalcones via a Consecutive One-Pot Reaction Catalyzed by Chiral Phosphoric Acid. / Park, Do Young; Lee, So Young; Jeon, Jiye; Cheon, Cheol-Hong.
In: Journal of Organic Chemistry, Vol. 83, No. 20, 19.10.2018, p. 12486-12495.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Enantioselective Synthesis of Tetrahydroquinolines from 2-Aminochalcones via a Consecutive One-Pot Reaction Catalyzed by Chiral Phosphoric Acid
AU - Park, Do Young
AU - Lee, So Young
AU - Jeon, Jiye
AU - Cheon, Cheol-Hong
PY - 2018/10/19
Y1 - 2018/10/19
N2 - A new asymmetric protocol for the synthesis of chiral tetrahydroquinolines from 2-aminochalcones via a two-step one-pot consecutive process (cyclization/asymmetric reduction) has been developed using chiral phosphoric acid as the sole catalyst. 2-Aminochalcones were converted into the corresponding quinolines through chiral phosphoric acid-catalyzed dehydrative cyclization, and the resultant quinolines were subsequently reduced to the chiral tetrahydroquinolines via chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester. Various 2-aminochalcones could be applicable to this protocol, and the desired tetrahydroquinolines were obtained in excellent yields and with excellent enantioselectivities. Furthermore, the utility of this protocol has been successfully demonstrated in the highly efficient synthesis of estrogen receptor modulator.
AB - A new asymmetric protocol for the synthesis of chiral tetrahydroquinolines from 2-aminochalcones via a two-step one-pot consecutive process (cyclization/asymmetric reduction) has been developed using chiral phosphoric acid as the sole catalyst. 2-Aminochalcones were converted into the corresponding quinolines through chiral phosphoric acid-catalyzed dehydrative cyclization, and the resultant quinolines were subsequently reduced to the chiral tetrahydroquinolines via chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester. Various 2-aminochalcones could be applicable to this protocol, and the desired tetrahydroquinolines were obtained in excellent yields and with excellent enantioselectivities. Furthermore, the utility of this protocol has been successfully demonstrated in the highly efficient synthesis of estrogen receptor modulator.
UR - http://www.scopus.com/inward/record.url?scp=85054924369&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85054924369&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b01709
DO - 10.1021/acs.joc.8b01709
M3 - Article
C2 - 30256637
AN - SCOPUS:85054924369
VL - 83
SP - 12486
EP - 12495
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -