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제118회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Small-­Molecule Ammonium Compounds as Enantioselective Catalysts and a Platform for Mechanitic Investigations

2016년 9월 1일 09시 39분 20초
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목 14시 : 50분
유기화학 - Current Trends in Organic Chemistry I: Methodology and Application
저자 및
Amir H. Hoveyda
Boston College, Merkert Chemistry Center, Chestnut Hill, Massacussetts, 02467, USA, Korea
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승인 1건
In this Lecture, small organic molecules that catalyze reactions of unsaturated organoboron reagents with imines and carbonyls will be introduced; products are amines and alcohols of high enantiomeric purity, intermediates used to synthesize many biologically active molecules. A distinguishing feature of the catalyst class is a proton embedded within their structure; the resulting electronic activation and structural organization play a key role in every stage of the carbon‐carbon bond forming processes; this includes achieving high rates of catalyst regeneration and product release, typically obtained through rapid ligand exchange with metal-­containing systems. The catalyst is derived from the abundant amino acid valine and may be prepared in large quantities in four steps with cheap chemicals. Reactions are scalable and do not demand stringent conditions and are complete within a few hours, furnishing products typically in >85% yield and ≥97:3 enantiomeric ratio (er). Moreover, it will be demonstrated that this catalyst class has been utilized for examination of key mechanistic principles that serve as the foundation for the development of versatile new methods. Among these is the use of catalyst-­controlled 1,3-­borotropic shifts in the development of diastereo- and enantioselective crotyl additions to imines and evaluation of various electrostatic interactions involving organofluorine compounds resulting in exceptionally efficient and selective allyl additions to fluoroketones.