臺灣博碩士論文加值系統

中文摘要
一.β-氨基,α,β-未飽和,γ-硫化環內酯之酸催化 Michael Addition反應研究
我們利用本實驗室發展的方法，合成起始物4-(1-pyrrolidinyl)-2(5H) thiophenone 1，並研究其應用於Michael加 成反應時，改變溶劑、反應溫度、反應時間及Michael acceptor對反應之影響，並利用HPLC技術來分析產物的非 鏡 像立體選擇性（diastereoselectivity）。
二. 掌性 Vinylogous Urethane之反式醛醇加成反應研究及合成應用
1. 我們利用含樟腦架構的掌性Vinylogous Urethane（VU）3與醛類化合物，進行掌性反式-醛醇加成反應，並 研究其反應狀況，得到之產物再利用HPLC之chiral column判斷其鏡像立體選擇性（enantioselectivity）。
2. 經醛醇加成反應所得的反式醛醇加成產物5，可用來合成天然物Bafilomycin A1之片斷prelactone B。

Abstract
一. Michael Addition Reaction of b-amino, a,b-unsaturated-g-thiolactone under Lewis acid conditions.
4-(1-pyrrolidinyl)-2(5H)thiophenon 1, which developed in our laboratory was used to study it''s Michael reaction under Lewis acid conditions. Their reaction products were analyzed using HPLC techniques to determine diastereoselectivity.
二.Chiral Anti-Aldol Reaction Studies of Chiral Vinylogous Urethane and their Application in Natural Product Synthesis.
1. Camphor derived chiral vinylogous urethane 3 was deprotonated and reacted with aldehyde to from anti-aldol product, the product selectivity was analyzed using chiral column to determine their enantioselectivity.
2. Product 5 was used to synthesize Bafilomycin A1 fragment prelactone B.

目 錄
中文摘要…………………………………...…………………………..Ⅰ
英文摘要……………………………………………………………….Ⅲ
誌謝……………………………………………….…………………….Ⅳ
目錄………………………………………………………….………….Ⅴ
一.β-氨基,α,β-未飽和,γ-硫化環內酯之酸催化Michael加成反應
之反應研究
1-1 導論……………………………………..………………..….…......1
1-2 結果與討論……………….……………………………..…........…8
1-3 結論……………………………………………………….…....…14
二. 掌性Vinylogous Urethane之反式-醛醇加成反應之反應研究
及合成應用
2-1 導論
2-1-1 簡單醛醇加成反應…………………..………………....................15
2-1-2 反式-醛醇加成反應………….……………………...….............…19
2-1-3 掌性反式-醛醇加成反應……………………..…….…..............…20
2-1-4 Vinylogous urethane 之反式-醛醇加成反應………....….........….....27
2-2 結果與討論……………………………………………...……..........32
2-3 合成之應用與絕對立體化學之決定………..……………..….........43
2-4 結論……………………..…………………………..………….........47
參考文獻……………………….…………..………….………….......…49
實驗部分一般敘述………………………..…………..………..…….…52
實驗步驟及光譜數據……………………..……….……..………..…….54
附錄
X-ray data…………………………........…..……..……………………….75
HPLC圖譜……………………………....……………………….…...…87
氫圖譜…………………………………....……………………………..94
碳圖譜……………………………………....………………….…...…113

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