銠金屬(I)/掌性雙環[2.2.1]雙烯配體催化進行不對稱1,4-加成反應：合成掌性γ-胺基酸及γ-胺基膦酸之應用

Enantioselective Synthesis of γ-Amino Acids and γ-Amino Phosphonic Acids via Rhodium Catalyzed Asymmetric 1,4-Conjugate Addition Reactions

黃志浩(Huang Chih-Hao)

指導教授 ： 吳學亮

國立臺灣師範大學/理學院/化學系/碩士(2016年)

https://doi.org/10.6345/NTNU202203622

摘要

['本論文研究主題為利用本實驗室所開發的掌性雙環[2.2.1]雙烯配體與一價銠金屬形成之催化劑催化芳香基硼酸與γ-位胺基及膦酸酯取代之α , β-不飽和酯類進行不對稱1,4-加成反應。使用三莫耳百分率的銠金屬試劑(3 mol% of Rh)及L1e或L1f配體催化加成反應進行，生成的產物其產率有26–>99%，鏡像超越值為90–>99.5% ee。這個合成方法可利用來合成balcofen及phaclofen藥物分子。']

關鍵字

銠金屬催化試劑 ； 掌性雙烯配基 ； α , β-不飽和羧酸酯

並列摘要

['This thesis describes an efficient synthesis of highly enantioenriched 4-amino-3-aryl-butanoates and 4-phosphoryl-3-aryl-butanoates via an enantioselective 1,4-addition of an array of aryboronic acids to γ-amino-α , β-unsaturated esters and γ-phosphoryl-α , β-unsaturated esters. In the presence of 3 mol% of the Rh(I)/ chiral diene L1e or L1f as catalyst, the conjugate addition adducts were isolated in 26–>99% yield and 90–>99.5% ee. The synthetic usefulness of the developed method was demonstrated in the syntheses of baclofen and phalcofen.']

並列關鍵字

Rhodium ； Chiral diene ligand ； α , β-Unsaturated esters

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