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thyan@mail.nchu.edu.tw

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有機化學

Organic Chemistry

 

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1.          B. S., National Chung Hsing University (1972)

2.          M. S., National Taiwan University (1976)

3.          Ph. D., Ohio State University (1982)

4.          Associate Professor, National Chung Hsing University (1983-1993)

5.          Professor, National Chung Hsing University (1993-)

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我的研究興趣包括研發手性試劑、建立新合成方法、以及不對稱合成天然物。本研究室先前已製備出高選擇性的手性鹼、手性亞硝、及手性烯醇鹽等反應試劑。我們已發展出以鈦-鎂金屬試劑為催化劑輔助「羰基」選擇性的轉換成烯、聯烯或烯醚。我們在「不對稱全合成」的一些研究努力表現在最近成功的合成前列腺素及生物鹼類。進一步的研究擴及於研發手性催化劑以及生物鹼類、克流感和紫杉醇的合成。

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My research interests include the development of chiral reagents, investigation of new synthetic methods, and asymmetric total synthesis of natural products.  Previous work in my group has prepared highly selective reagents such as chiral bases, chiral nitrosos, and chiral enolates.  Recently, we established the feasibility of TiCl4 -Mg-CH2 Cl2 system as a novel class of ambiphilic carbenoid equivalents to effect selected transformations of carbonyl groups to alkenes, enol ethers, or cyclopropanes.  The successful syntheses of prostaglandins and narcissus alkaloids typify our activity in the asymmetric total synthesis.  Additional studies aimed at elaborating the chiral catalysts and the synthesis of drugs like lycorine alkaloids, oseltamivir (tamiflu), aminocyclitol unit valienamine, and taxol.

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A.    Publications:

1.      Kuo-Wei Lin, Chi-Hui Tsai, I-Lin Hsieh, and Tu-Hsin Yan*, “New, General, and Practical Preparation of Methyl Ketones via the Direct Coupling of Amides with CH2Cl2 Promoted by TiCl4 /Mg”, Org. Lett., 2008, 1927-1930.

2.      Kuo-Wei Lin, Cheng-Yih Chen, Wei-Fan Chen, and Yan*, T.-H., “A New Entry to 1,5-Keto Esters and Their 4,4-Dideuterio Derivatives via Methylene Chloride as “Methylene Dianion” Equivalents” , J. Org. Chem., 2008, 73, 4759-4761.

3.      Tsai, C.-C.; Hsieh, I.-L.; Cheng, T.-T.; Tsai, P.-K.; Lin, K.-W.; Yan*, T.-H., “New, General, and Practical Enamine-Cyclopropanation Using a Dichloromethane”, Org. Lett., 2006, 2261-2263.

4.      Lin, K.-W.; Yan, S.; Hsieh, I.-L. Yan*, T.-H., “Unusual Ambiphilic Carbenoid Equivalent in Amide-Cyclopropanation”, Org. Lett., 2006, 2265-2267.

5.      Cheng, T.-T.; Tsai, C.-C.; Tsai. C.-H.; Chang T.-Y.; Tsai, P.-K.; Wang, Y.-C.; Yan*, T.-H., “Novel Ambiphilic Dichlorocarbenoids Equivalent in Alkene Cyclopropanation and Carbonyl Olefination”, J.Org.Chem., 2006,71,4324-4327.

6.      Yan, T.-H.; Tsai, C.-C.; Chien, C.-T.; Cho, C.-C.; Huang, P.-C.  “Dichloromethane Activation.  Direct Methylenation of Ketones and Aldehydes with CH2Cl2 Promoted by Mg/TiCl4/THF”, Org. Lett. 2004, 4961-4963.

7.      Yan, T.-H.; Chien, C.-T.; Tsai, C.-C.; Lin, K.-W.; Wu, Y.-H.  “Dichloromethane as an Unusual Methylene Equivalent.  A New Entry of Highly Nucleophilic and Selective Titanium-Methylene-Complexes for Ester Methylenation”, Org. Lett. 2004, 4965-4967.

8.      Elango, S.; Yan, T.-H. "A Short Synthesis of (+)-Narciclasine via a Strategy Derived from Stereocontrolled Epoxide Formation and SnCl4-Catalyzed Arene-Epoxide Coupling", J. Org. Chem. 2002, 67, 6954-6959.

9.      Elango, S.; Yan, T.-H. "A Short Synthesis of (+)-Lycoricidine", Tetrahedron, 2002, 58, 7335-7338.

10.  Wang, Y.-C.; Lu, T-M.; Elango, S.; Lin, C.-C.; Tsai, C.-T.; Yan, T.-H. "Switch in Asymmetric Induction Sense in Cycloadditions Using Camphor-Based Nitroso Dienophiles", Tetrahedron:  Asymmetry, 2002, 13, 691-695.

11.  Elango, S.; Wang, Y.-C.; Cheng, C.-L.; Yan, T.-H. "Prparation and conversion of chiral O-isopropylidene-protected 4-aminocyclohexenol to various key intermediates toward narcissus alkaloids", Tetrahedron Lett. 2002, 43, 3757.

12.  Wang, Y.-C.; Yan, T.-H. "Al-Hg Promoted Chemoselective Dehalogenation of Halohydrin Aldol Adducts", J. Chem. Soc. Chem. commun. 2000, 545-546.

13.  Wang, Y.-C.; Huang, C.-Y; Chen, Y.-C.; Chuang, S.-C.; Yan, T.-H. "A Facile Method for the Synthesis of Enantiopure a-Unsubstituted b-Hydroxy Esters", Tetrahedron:  Asymmetry, 2000, 11, 1797-1800.

14.  Wang, Y.-C.; Yan, T.-H. "A New Approach for the Chemoselective Debromination of Chiral Bromohydrins.  Toward the Development of a Very General Approach to Enantiopure a-Unsubstituted b-Hydroxy acids", J. Org. Chem. 2000, 65, 6752-6755.

B.     Conference Paper:

1.      "Methods for the Construction of the Typical Framework of Narcissus Alkaloid," Yan, T.-H. Oral presentation at Taipei: Frontiers In Organic Chemistry- A Symposium Dedicated to the Memory of Prof. Ta-Shue Chou, February 14, 2004.

2.      "Methods for the Construction of the Typical Framework of Narcissus Alkaloid," Yan, T.-H. Oral presentation at Kaohsiung: International Symposium on Organic Reactions, December 18-21, 2003.

國立中興大學化學系National Chung Hsing University Department of Chemistry

地址:台中市國光路250號 化學館 電話:04-22840411 傳真:04-22862547