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117th General Meeting of Korean Chemical Society A self-healing catalyst system: ppm-level catalyst loading organocatalyzed enantioselective silylation of alcohols

Submission Date :
3 / 23 / 2016 , 15 : 44 : 45
Abstract Number :
Presenting Type:
Oral Presentation
Presenting Area :
한국다우케미칼 우수논문상 수상자 구두발표
Authors :
박상연, 이지웅, 송충의*
성균관대학교 화학과, Korea
Assigned Code :
KCS2.O-4 Assigend Code Guideline
Presenting Time :
THU, 10 : 54

Catalysis, in principle, should offer an infinite turnover number for a desired chemical transformation by regenerating the catalyst without altering its molecular-level structure and physicochemical properties. However, limitations arise from different deactivation mechanisms and catalyst poisoning by chemical impurities and/or side products, lowering the lifetime of catalytically active species.
The field of organocatalysis has blossomed over the past few decades, becoming an alternative to transition-metal catalysis or even replacing the realm of transition-metal catalysis. However, a truly powerful organocatalyst with a high turnover number and turnover frequency while retaining high enantioselectivity is yet to be discovered. Despite many efforts, the current limit of catalyst loading for asymmetric organocatalysis is usually in the range of 0.1–1 mol% for overriding of the non-selective background pathway. Similar to metal catalysis, thus, extremely low catalyst loading (ppm or ppb levels) is the ultimate goal of the organocatalysis community.
Quite recently, we developed ppm-level loading asymmetric hydrogen-bond catalysis by designing an in-situ repairable catalyst system.1 For example, in the presence of catalyst healing agents (e.g., KF and Amberlite CG-50), 1 ppm loading of our chiral oligoethylene glycol catalyst was enough to achieve highly enantioselective silylation of functionally unbiased alcohols.