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| Type |
Symposium |
| Area |
Current Trends in Organic Chemistry III: Enabling Methodologies |
| Room No. |
Halla Hall B |
| Time |
FRI 15:45-: |
| Code |
ORGN3-3 |
| Subject |
Proline-Derived Organocatalysts; Design, Synthesis and Applications |
| Authors |
Do Hyun Ryu
Department of Chemistry, Sungkyunkwan University, Korea |
| Abstract |
Interest in organocatalysis has increased over the past several decades. Many useful organocatalysts have been developed and prepared from easily accessible natural products. Among them, many efforts have been made to devise new catalysts based on L-proline structure.
Our group has developed prolinol derived chiral oxazaborolidinium ion (COBI) as a Lewis acid. They have been proven as effective catalysts for various asymmetric reactions with diazo compounds.
Recently, we developed a series of novel L-proline derived tertiary amine bifunctional organocatalysts, which were successfully applied to the asymmetric Michael addition reactions of β-nitroolefins using dithiomalonates or 2-oxochroman-3-carboxylate esters as Michael-donors. The reaction proceeded in high yields (up to >99%) with high enantioselectivities (up to >99% ee). Additionally, a biomimetic synthesis of chiral 3,4-dihydropyranones through Michael addition/lactonization reaction cascade of thioesters and β,γ-unsaturated α-keto esters was developed. The mechanism was demonstrated by DFT calculation and the utility of the products was shown in the formal synthesis of anti-hypercholesterolemic agent.
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| E-mail |
dhryu@skku.edu |
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121st General Meeting of the KCS