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제126회 대한화학회 학술발표회 및 총회 Mechanism-Driven C-H Amidation: Reaction Development and Asymmetric Catalysis

등록일
2020년 8월 28일 16시 06분 41초
접수번호
0119
발표코드
KCS1-2 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
월 14시 : 10분
발표형식
심포지엄
발표분야
KCS - [International Symposium] The Future is Already Here: Advancing Frontiers in Chemical Research
저자 및
공동저자
Sukbok Chang
Department of Chemistry, Institue for Basic Scicence and Korea Advanced Institute of Science and Technology, Korea
Direct amidation of C–H bonds is a highly desirable reaction considering high utility of amidated products in total synthesis, medicinal chemistry and materials science. Although tremendous research efforts have been made especially in recent years, the current status enabling such C–H reactions in excellent stereoselectivity and high efficiency is still rather limited. In this context, we have developed a novel methodology that employs tailor-made Ir-based catalysts in combination with dioxazolone substrates to access a short-lived metal-nitrenoid intermediate, thereby eventually leading to a construction of γ-lactams via an outer-sphere C–H insertion pathway. The scope was found to be broad and a range of carboxylic acids could be readily utilized for the lactam formation. Indeed, the power of this new method was demonstrated in the successful late-stage functionalization of bio-active molecules to produce molecules that are highly sought after for pharmaceutical applications. More recently, we have successfully introduced an iridium-based catalyst system for asymmetric C−H amidation that enables facile construction of chiral γ-lactams starting from commodity chemicals. Various types of secondary C−H bonds, such as being positioned at the benzylic, unactivated aliphatic, propargylic, and allylic sites, were all smoothly reacted in a regio- and stereoselective manner. The present approach will find broad applications in medicinal chemistry, and the mechanistic insights may provoke further developments in related asymmetric catalysis.

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