本論文研究主要分為兩部分，第一部分我們成功地利用Seyferth-Gilbert 試劑在二環[4.3.0]-1,5-二氮-5-十一烯(DBU)的促進下與溴化物進行取代反應可廣泛合成予體/受體類型的重氮膦酸酯化合物，有別於以往的文獻須利用希夫鹼與亞膦酸二甲酯做縮合反應，我們反倒能保留住此敏感性羰基於分子結構上。
第二部分則將上述所合成的α-重氮化合物藉由銠金屬卡賓體分子間的氮-氫鍵插入反應轉化為各類型同時具有醛基、酮基、酯基及醯胺基的α-胺基膦酯合物。在電子效應層面上，α-重氮化合物上推、拉電子基效應對產率影響並不明顯，可達致79 - 98%；而在作為胺基來源的苯胺上則是拉電子基效應比較佳，我們推測此反應機構偏向於協同反應路徑(concerted)而非逐步路徑(stepwise)。此外在立體障礙及結構層面上，若重氮官能基明顯裸露則易於與銠金屬反應可提升反應性。
藉由此有效率的兩步驟反應，我們能夠廣泛合成出四十種以上各類型的胺基膦酸酯化合物，其中包含五種丙胺酸(Phe)、色胺酸(Try)、酪胺酸(Tyr)、天門冬醯胺(Asn)及天冬胺酸(Asp)等天然胺基酸所對應的α-胺基膦酸酯化合物，此外若以鄰甲基苯胺(o-toluidine)取代苯胺則最後可利用三氯異氰脲(trichloroisocyanuric acid)去除保護基而得到胺基膦酸鹽類。

The two continuous reactions were included in the thesis for the synthesis of various α-aminophosphonates. In the first reaction, we successfully synthesized extensive donor/acceptor diazo phosphate compounds through the bromo-substitution with the Seyferth-Gilbert reagent under the activation of bicyclo[4.3.0]-1,5-diaza-5-undecene (DBU). This method avoided the requirement of Schiff base formation in other literatures and reserved the sensitive carbonyl groups on the chemical structures.

The synthesized -diazoalkylphosphonates were then appealed to the intermolecular N-H insertion reaction with rhodium carbenoid and aniline to from the α-aminophosphonates with the tolerance of aldehyde, ketone, ester, and amide functional groups. The electronic effect on the -diazophosphonates was not obvious and steadily gave moderate to excellent yield (79-98%). However, the deactivating but electron-releasing groups on the aniline seemed to deliver better yield. We concluded the mechanism might undergo the concerted route rather than the stepwise one and the steric effect promote the access of the diazo compounds to the rhodium metal would increase the reaction rate and yield.

According to the two-steps strategy, we successfully synthesized 40 kinds of α-aminophosphate compounds including five phosphonate derivatives of natural amino acids such as phenylalanine, tryptophan, tyrosine, asparagine, and aspartic acid. Instead of aniline, the cleavable o-toluidine could afford the aminophosphonic hydrochloride salt with the treatment of trichloroisocyanuric acid.

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