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제117회 대한화학회 학술발표회, 총회 및 기기전시회 A self-healing catalyst system: ppm-level catalyst loading organocatalyzed enantioselective silylation of alcohols

2016년 3월 23일 15시 44분 45초
KCS2.O-4 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
목 10시 : 54분
한국다우케미칼 우수논문상 수상자 구두발표
저자 및
박상연, 이지웅, 송충의*
성균관대학교 화학과, Korea

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.