|
|
| Type |
Poster Presentation |
| Area |
Organic Chemistry |
| Room No. |
Event Hall |
| Time |
4월 19일 (목요일) 11:00~12:30 |
| Code |
ORGN.P-421 |
| Subject |
Enantioselective Synthesis of 2-Substituted Tetrahydroquinoline via Bifunctional Chiral Phosphoric Acid-catalyzed Cascade Reaction of 2-Aminostyryl ketones |
| Authors |
Do Young Park, So Young Lee, Jiye Jeon, Cheol-Hong Cheon*
Department of Chemistry, Korea University, Korea
|
| Abstract |
The development of novel methods for the synthesis of optically active compounds through combining more than two catalytic transformations in one pot has received a considerable attention. However, there have been always problems associated with compatibility between the each catalytic system. Alternatively, if cascade reactions were developed with a single catalyst utilizing its mechanically distinct activations, the efficiency of these transformations could be considerably improved since this approach could eliminate the compatibility issues between different catalytic systems. Despite this apparent advantages of a cascade reaction with a single catalyst, there have been very limited number of examples reported in the literature and further studies are needed on organo-bifunctional catalyst.
Herein, we describe the development of a novel protocol for the synthesis of chiral tetrahydroquinolines from 2-aminostyryl ketones using the bifunctionality of a chiral phosphoric acid as a cascade catalyst. 2-Aminostyryl ketones could be converted to the corresponding quinolines using the Lewis basic nature of chiral phosphoric acid and the resulting quinolines could be further reduced to the tetrahydroquinolines with Hantzsch ester based on the Brønsted acid nature of chiral phosphoric acid. Various 2-aminostyryl ketones could be applicable to this catalytic cascade system and the desired tetrahydroduqinolines were obtained in excellent yields and enantioselectivities.
|
| E-mail |
bluesky7409@naver.com |
|
121st General Meeting of the KCS