經由Sulfa-Michael/Amino-cyclization/Acetalization非鏡像選擇性合成外消旋呋喃[2,3-e][1,4]噻嗪酮架構
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2018
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本文利用有機分子進行有機反應，發展具有高非鏡像選擇性之官能基的呋喃噻嗪酮結構。本實驗利用1,3-茚滿二酮 (三氟甲基)與2-胺基苯硫酚為起始物，在沒有催化劑的條件下，進行Sulfa-Michael/amino-cyclization/acetalization反應，得到多取代的呋喃[2,3,e][1,4]噻嗪酮結構，並同時建立三個四級碳及四個立體中心，具有傑出的產率(高達95%)及優異的非鏡像選擇性(高達 >20:1)。此外，也經由單晶繞射X-ray確認其產物的相對立體組態；也期許本實驗可應用在天然物合成及相關生物應用方面。
Abstract In this thesis, organic molecules were used for organic reactions to develop furothiazinone structures with diastereoselective functionalized groups. In this experiment, Sulfa-Michael/amino-cyclization/acetalization reaction was performed by using 1,3-indanedione (trifluoromethyl) and 2-aminothiophenol as the initial starting materials in the absence of a catalyst. Multi-substituted furo[2,3,e][1,4]thiazinone structure, and the simultaneous establishment of three quaternary carbons and four stereocenters, with excellent yields (up to 95%) and diastereoselectivities (up to >20:1). In addition, the corresponding relative three-dimensional configuration of the product was also confirmed via single crystal diffraction X-ray; it is also expected that this experiment can be applied in the synthesis of natural products and related biological applications.
Abstract In this thesis, organic molecules were used for organic reactions to develop furothiazinone structures with diastereoselective functionalized groups. In this experiment, Sulfa-Michael/amino-cyclization/acetalization reaction was performed by using 1,3-indanedione (trifluoromethyl) and 2-aminothiophenol as the initial starting materials in the absence of a catalyst. Multi-substituted furo[2,3,e][1,4]thiazinone structure, and the simultaneous establishment of three quaternary carbons and four stereocenters, with excellent yields (up to 95%) and diastereoselectivities (up to >20:1). In addition, the corresponding relative three-dimensional configuration of the product was also confirmed via single crystal diffraction X-ray; it is also expected that this experiment can be applied in the synthesis of natural products and related biological applications.
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硫麥克加成反應, 胺環化反應, 縮醛反應, 呋喃噻嗪酮, Sulfa-Michael addition, amino-cyclization, acetalization, furothiazinone