銠金屬(I)結合掌性雙環[2.2.1]雙烯配體進行不對稱加成催化反應：合成掌性α-及β2-胺基酸及其衍生化合物之應用
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2020
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Abstract
本論文利用銠金屬催化試劑針對去氫丙胺酸107、113或β取代硝基烯酸酯128進行一系列不對稱加成反應，可以得到具有高產率與良好鏡像超越值之加成產物。並且透過同位素實驗以及DFT理論計算推測其催化反應路徑中的配基效應、質子化步驟和立體效應。此方法能夠有效合成出掌性α-或β2-胺基酸及其衍生物。
A highly enantioselective rhodium-catalyzed conjugate addition reactions of dehydroalanines 107, 113 and β-nitroacrylates 128 with a variety of aryl boronic acids is described, providing an access to both chiral α- and β2-amino acid derivatives in good yields and enantioselectivities. Mechanistic studies which include deuterium labelling experiments and DFT calculations supported the ligand-assisted, protonation step and the stereochemical effect of mechanism. Thses method were applied for the synthesis of α-and β2-amino acid derivatives.
A highly enantioselective rhodium-catalyzed conjugate addition reactions of dehydroalanines 107, 113 and β-nitroacrylates 128 with a variety of aryl boronic acids is described, providing an access to both chiral α- and β2-amino acid derivatives in good yields and enantioselectivities. Mechanistic studies which include deuterium labelling experiments and DFT calculations supported the ligand-assisted, protonation step and the stereochemical effect of mechanism. Thses method were applied for the synthesis of α-and β2-amino acid derivatives.
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銠金屬催化試劑, 胺基酸, 加成反應, rhodium-catalyzed, amino acid, conjugate addition