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  • 08월 28일 16시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

Enantioselective Desymmetrization of 2-Substituted Glycerols

2008년 8월 21일 11시 40분 33초
목16A1심 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
목 14시 : 20분
유기화학 - Diversity in Organic Chemistry (Organic Synthesis and Synthetic Method)
저자 및
한국과학기술원 화학과, Korea
Asymmetric formation of quaternary carbon centers is considered as one of the most challenging functionalizations in synthetic organic chemistry. In particular, the centers including amino and hydroxyl functional groups are intriguing because they are found in a variety of biologically potent natural and artificial compounds. Due to their synthetic values as building blocks, much effort has been exerted to explore their stereoselective preparation. The asymmetric synthesis of tertiary alcohols has frequently resorted to epoxidation and dihydroxylation. In recent years, several nucleophilic addition reactions to ketones have emerged to secure the enantiomerically enriched corresponding tertiary alcohols, which comprise cyanide addition, aldol condensation, alkylzinc addition and epoxide opening. If the chiral quaternary building blocks can be generated from meso stereoisomers by asymmetric desymmetrization, the synthetic route is conceivably useful and versatile. Although the desymmetrization has been sometimes implemented to resolve meso compounds, their prostereogenic centers are mostly tertiary but rarely quaternary. It is of remarkable value to extend the desymmetric method to the enantioselective synthesis of the alcohols. In this presentation, we will discuss the desymmetric approaches to the chiral quaternary carbons and their synthethetic application to some of the physiologically significant compounds such as ZD 0870 (triazole antifungal), azithromycin and dysiherbaine.