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研究生：	方若嫙 Fang, Jo-Hsuan
論文名稱：	以掌性銠金屬雙烯錯合物催化不對稱1,4-加成反應合成掌性含氮分子 Syntheses of Chiral Nitrogen-containing Molecules via Asymmetric 1,4-Addition Reactions Catalyzed by Rhodium/Chiral Diene Complexes
指導教授：	吳學亮 Wu, Hsyueh-Liang
學位類別：	博士 Doctor
系所名稱：	化學系 Department of Chemistry
論文出版年：	2016
畢業學年度：	105
語文別：	中文
論文頁數：	314
中文關鍵詞：	鏡像選擇性、掌性二烯配體、銠催化、不對稱合成、共軛加成、芳基硼酸、β-胜肽
英文關鍵詞：	Enantioselective, Chiral diene ligands, Rhodium-catalyzed, Asymmetric synthesis, Conjugate addition, Arylboronic acids, β-Peptides
DOI URL：	https://doi.org/10.6345/NTNU202203482
論文種類：	學術論文
相關次數：	點閱：144 下載：0
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壹、銠催化芳基硼酸與氮-特丁氧羰基保護的α,β-不飽和γ-內醯胺的不對稱1,4-加成反應：
我們運用由左旋醋酸冰片酯合成出的一系列掌性雙環[2.2.1]二烯配體L1與一價銠金屬形成之催化劑，催化各種芳基硼酸14與氮-特丁氧羰基保護的α,β-不飽和γ-內醯胺195a進行不對稱1,4-加成反應。在0.5 mol%的Rh(I)/L1f催化劑量下，本反應可生成高產率（31–>99%）及高鏡像選擇性（93–>99.5% ee）的加成產物(R)-197。此法可應用至苯基海人酸207以及MCHR1拮抗劑302的形式合成。

貳、銠催化芳基硼酸與α-取代的β-硝基丙烯酸酯的不對稱1,4-加成反應：
本部分內容綜述各種芳基硼酸14與α-取代的β-硝基丙烯酸酯361的不對稱共軛加成反應。以5.0 mol%的Rh(I)/L1e進行催化反應，並利用KHF2做為添加劑，可製備出加成產物(R)-362，產率最高可至63%，鏡像超越值高達99% ee。此方法可應用至具有光學活性的β2,2-胺基酸369，β-內醯胺375，以及α,β2,2,α-胜肽380的不對稱合成。

I.Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to N-Boc Protected α,β-Unsaturated γ-Lactam:
A family of chiral bicyclo[2.2.1]heptadiene ligands L1 synthesized from L-(−)-bornyl acetate were utilized in the Rh(I)-catalyzed enantio- selective 1,4-addition of various arylboronic acids 14 to N-Boc-protected α,β-unsaturated γ-lactam 195a. In the presence of 0.5 mol% of a Rh(I)/L1f catalyst, the corresponding adducts (R)-197 were isolated in high yields (31–>99%) and excellent enantioselectivities (93–>99.5% ee). This metho- dology was employed for the formal synthesis of phenylkainic acid 207 and MCHR1 antagonist 302.

II.Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α-Substituted β-Nitroacrylates:
Asymmetric conjugate addition of various arylboronic acids 14 to α-substituted β-nitroacrylates 361 was described. The reaction, catalyzed by 5.0 mol% of Rh(I)/L1e, provided the conjugate adduct (R)-362 in up to 63% yield and up to 99% ee using KHF2 as an additive. This method are applied to the asymmetric synthesis of optically active β2,2-amino acid 369, β-lactam 375, and α,β2,2,α-peptide 380.

摘要．．．．．．．．．．．．．．．．．．．．．．．．．．．．　i
Abstract．．．．．．．．．．．．．．．．．．．．．．．．．　iii
目錄．．．．．．．．．．．．．．．．．．．．．．．．．．．．　v
圖目錄．．．．．．．．．．．．．．．．．．．．．．．．．．．　xi
流程圖目錄．．．．．．．．．．．．．．．．．．．．．．．．　xiii
表目錄．．．．．．．．．．．．．．．．．．．．．．．．．．　xxi
附圖目錄．．．．．．．．．．．．．．．．．．．．．．．．．　xxv
中英文縮寫名稱對照表．．．．．．．．．．．．．．．．．．　xxxix

第一章　緒論．．．．．．．．．．．．．．．．．．．．．．．．　1
第二章　過渡金屬催化有機合成反應．．．．．．．．．．．．．．　9
　　第一節　前言．．．．．．．．．．．．．．．．．．．．．．　9
　　第二節　有機金屬化學簡介．．．．．．．．．．．．．．．．　9
　　第三節　過渡金屬催化反應．．．．．．．．．．．．．．．．　10
　　第四節　過渡金屬催化循環機制．．．．．．．．．．．．．．　11
　　第五節　有機合成試劑發展．．．．．．．．．．．．．．．．　15
　　第六節　結論．．．．．．．．．．．．．．．．．．．．．．　16
第三章　銠催化的不對稱共軛加成反應．．．．．．．．．．．．．　17
　　第一節　前言．．．．．．．．．．．．．．．．．．．．．．　17
　　第二節　文獻回顧．．．．．．．．．．．．．．．．．．．．　17
一、    α,β-不飽和羰基化合物的ECA反應．．．．．．．．．．　17
二、    鏡像選擇性反應立體化學路徑．．．．．．．．．．．．　29
三、    掌性雙環二烯配體的開發與應用．．．．．．．．．．．　31
四、    掌性雙環二烯配體在銠催化不對稱合成上的應用．．．．　41
　　第三節　實驗概念與設計．．．．．．．．．．．．．．．．．　67
　　第四節　實驗結果與討論．．．．．．．．．．．．．．．．．　71
一、    α,β-不飽和酯之製備．．．．．．．．．．．．．．．．　71
二、    α,β-不飽和酯的ECA反應．．．．．．．．．．．．．．　72
三、    推測α,β-不飽和酯的銠催化ECA反應途徑．．．．．．．　79
　　第五節　結論．．．．．．．．．．．．．．．．．．．．．．　80
第四章　銠催化不對稱1,4-加成反應製備掌性4-芳基-2-吡咯啶酮．　81
　　第一節　前言．．．．．．．．．．．．．．．．．．．．．．　81
　　第二節　文獻回顧．．．．．．．．．．．．．．．．．．．．　82
一、    掌性4-芳基-2-吡咯啶酮的建構方式及合成應用．．．．　82
二、    α,β-不飽和γ-內醯胺的ECA反應與應用．．．．．．．．　94
　　第三節　實驗概念與設計．．．．．．．．．．．．．．．．．　97
　　第四節　實驗結果與討論．．．．．．．．．．．．．．．．．　98
一、    α,β-不飽和γ-內醯胺之合成．．．．．．．．．．．．．　98
二、    α,β-不飽和γ-內醯胺的ECA反應．．．．．．．．．．．　99
三、    推測α,β-不飽和γ-內醯胺的ECA反應途徑．．．．．．．　109
　　第五節　結論．．．．．．．．．．．．．．．．．．．．．　112
第五章　苯基海人酸的形式合成．．．．．．．．．．．．．．．　113
　　第一節　前言．．．．．．．．．．．．．．．．．．．．．　113
　　第二節　文獻回顧．．．．．．．．．．．．．．．．．．．　114
　　第三節　實驗概念與設計．．．．．．．．．．．．．．．．　123
　　第四節　實驗結果與討論．．．．．．．．．．．．．．．．　124
　　第五節　結論．．．．．．．．．．．．．．．．．．．．．　132
第六章　MCHR1拮抗劑的形式合成．．．．．．．．．．．．．．　133
　　第一節　前言．．．．．．．．．．．．．．．．．．．．．　133
　　第二節　文獻回顧．．．．．．．．．．．．．．．．．．．　134
　　第三節　實驗概念與設計．．．．．．．．．．．．．．．．　136
　　第四節　實驗結果與討論．．．．．．．．．．．．．．．．　137
　　第五節　結論．．．．．．．．．．．．．．．．．．．．．　144
第七章　銠催化不對稱1,4-加成反應製備掌性硝基丙酸酯．．．．　145
　　第一節　前言．．．．．．．．．．．．．．．．．．．．．　145
　　第二節　文獻回顧．．．．．．．．．．．．．．．．．．．　146
一、    掌性硝基丙酸酯的建構．．．．．．．．．．．．．．．　146
二、    β2,2-胺基酸四級立體中心的建構．．．．．．．．．．　149
　　第三節　實驗概念與設計．．．．．．．．．．．．．．．．　151
　　第四節　實驗結果與討論．．．．．．．．．．．．．．．．　153
一、    β-硝基丙烯酸酯化合物之合成．．．．．．．．．．．　153
二、    β-硝基丙烯酸酯之銠催化ECA反應．．．．．．．．．．　157
三、    掌性3-硝基-2-芳基丙酸酯的合成應用．．．．．．．．　174
四、    推測β-硝基丙烯酸酯的銠催化ECA反應途徑．．．．．．　179
　　第五節　結論．．．．．．．．．．．．．．．．．．．．．　184
第八章　總結論．．．．．．．．．．．．．．．．．．．．．．　185
第九章　實驗部分．．．．．．．．．．．．．．．．．．．．．　187
　　第一節　分析儀器及基本實驗操作．．．．．．．．．．．．　187
　　第二節　α,β-不飽和羰基化合物．．．．．．．．．．．．．　191
一、    α,β-不飽和酮與酯之合成．．．．．．．．．．．．．　191
二、    α,β-不飽和酯化合物之加成．．．．．．．．．．．．　197
　　第三節　α,β-不飽和γ-內醯胺化合物．．．．．．．．．．．　199
一、    α,β-不飽和γ-內醯胺之合成．．．．．．．．．．．．　199
二、    α,β-不飽和γ-內醯胺之加成．．．．．．．．．．．．　202
三、    苯基異海人酸的形式合成．．．．．．．．．．．．．．　228
四、    MCHR1拮抗劑的形式合成．．．．．．．．．．．．．．　230
　　第四節　β-硝基丙烯酸酯化合物．．．．．．．．．．．．．　235
一、    β-硝基丙烯酸酯之合成．．．．．．．．．．．．．．　235
二、    β-硝基丙烯酸酯之加成．．．．．．．．．．．．．．　247
三、    β2,2-胺基酸和β-內醯胺及α,β2,2,α-胜肽的合成．．　272
　　第五節　其他研究．．．．．．．．．．．．．．．．．．．　281
一、    氮-二苯基磷芳香亞胺之合成．．．．．．．．．．．．　281
二、    烯基硼酸頻哪醇酯之合成．．．．．．．．．．．．．．　282
第十章　參考文獻．．．．．．．．．．．．．．．．．．．．．　287

附錄一　X-光單晶數據與ORTEP解析圖譜．．．．．．．．．．　- 1 -
附錄二　核磁共振光譜圖．．．．．．．．．．．．．．．．　- 41 -
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