Lu, Yixin - National University of Singapore - Department of Chemistry, Faculty of Science

个人简介

Prof. Yixin Lu studied chemistry and received his B.Sc. from Fudan University, and continued his graduate studies in Canada and obtained his Ph.D. in Organic Chemistry under the supervision of Prof. George Just from McGill University in 2000. He then carried out his postdoctoral research with Prof. Peter W. Schiller at Clinical Research Institute of Montreal, and subsequently worked as an RCMS fellow with Prof. Ryoji Noyori at Nagoya University. In September 2003, He started his independent career and joined the National University of Singapore (NUS) where he is now a full professor. He was the recipient of a number of awards, including: Asian Core Program (ACP) Lectureship Awards to China, Japan, Korea and Taiwan (2009-2016); Young/Outstanding Scientist Award from the Faculty of Science, NUS (2009, 2013); GSK-SNIC Award in Organic Chemistry (2013); Dean’s Chair Professorship (2013). He is an Editorial Advisory Board Member for Accounts of Chemical Research, and Editorial Board Member for Aisan Journal of Organic Chemistry..

研究领域

ASYMMETRIC CATALYSIS AND SYNTHESIS Our group has keen interests in asymmetric catalysis/synthesis. Currently, the focus has been placed in developing enantioselective processes that can be promoted by small organic molecules. In particular, we are interested in devising highly efficient and versatile catalytic systems that can be readily derived from the chiral pools, and intend to apply our methodologies for the preparation of biologically important and synthetically useful molecules. Amino catalysis promoted by primary amino acids/amines L-Proline and its analogues have been predominantly used in amino catalysis. We initiated a research program in which primary amino acids/amines, rather than the secondary pyrrolidine moiety, were utilized as the catalyst for a range of important asymmetric transformations. We demonstrated that primary amine organic catalysts have often shown to be complementary or superior, in comparison with secondary amine-mediated processes. For instance, we discovered that natural tryptophan and silylated threonine were efficient catalysts for the direct aldol and Mannich reaction in aqueous media, respectively. Amino acid-derived novel tertiary amine-thiourea bifunctional catalysts Amino acids are probably the most readily available, most versatile and most economical chiral building blocks available to chemists, therefore, we were intrigued by the possibility of deriving a wide array of novel bi(multi)functional organocatalysts from simple amino acid structural scaffolds. To test our hypothesis, we designed tryptophan-based bifunctional thiourea catalysts and applied such catalysts to asymmetric Mannich reaction of fluorinated ketoesters. More recently, this concept has been extended, and more catalysts of this nature and more enantioselective reactions have been developed. Novel amino acid-incorporating multifunctional catalysts By incorporating amino acid residues into the existing bifunctional catalyst scaffolds, we derivatized novel multifunctional catalysts, and their effectiveness has been demonstrated in the enantioselective conjugate addition of oxindoles to a vinyl sulfone. We have recently shown wide applications of such catalysts in a number of enantioselective transformations. Novel bifunctional phosphines derived from amino acids/peptides Very recently, we questioned the possibility of deriving novel chiral phosphines from amino acids/peptides, and in this context, we have developed a number of bifunctional phosphines that can be readily derived from natural amino acids and peptides. Our catalytic systems have been applied to enantioselective (aza)-Morita-Baylis-Hillman reactions, [3+2] cycloadditions, [4+2] cycloadditions, and allylic alkylations, among others. MEDICINAL CHEMISTRY Organic chemistry has played a central role in pharmaceutical industry and drug discovery. We are exploring certain therapeutic areas by approaches combining organic synthesis, structure-based drug design and computational chemistry. Specifically, we are interested in the development of novel opioid peptides/opiates, and potentially useful anti-cancer agents.

近期论文

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Ni, H.; Tang, X.; Zheng, R.; Yao, W.; Ullah, N.; Lu, Y. "Enantioselective Phosphine-Catalyzed Formal [4+4] Annulation of a,b-Unsaturated Imines and Allene Ketones: Construction of Eight-Membered Rings", Angew. Chem. Int. Ed. 2017, 56, in press. Yao, W.; Dou, X.; Wen, S.; Wu, J.; Vittal, J. J.; Lu, Y. "Enantioselective Desymmetrization of Cyclohexadienones via an Intramolecular Rauhut�Currier Reaction of Allenoates", Nat. Commun. 2016, 7, 13024. Wang, T.; Han, X.; Zhong, F.; Yao, W.; Lu, Y. "Amino Acid-derived Bifunctional Phosphines for Enantioselective Transformations", Acc. Chem. Res. 2016, 49, 1329. (one of the Most Read Articles in July/August 2016) Dou, X.; Lu, Y.; Hayashi, T. "Base Free Conditions for Rhodium-Catalyzed Asymmetric Arylation to Produce Stereochemically Labile a-Aryl Ketones", Angew. Chem. Int. Ed. 2016, 55, 6739. Han, X.; Chan, W.-L.; Yao, W.; Wang, Y.; Lu, Y "Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates", Angew. Chem. Int. Ed. 2016, 55, 6492. Wang, T.; Yu, Z.; Hoon, D. L.; Phee, C. Y.; Lan, Y.; Lu, Y. "Regiodivergent Enantioselective g-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of a,a-Disubstituted a-Amino Acids and N,O-Acetal Derivatives", J. Am. Chem. Soc. 2016, 138, 265. (highlighted in SYNFACTS 2016, 309) Xu, L.-W.; Chen, Y.; Lu, Y. "Catalytic Silylations of Alcohols: Turning Simple Protecting-Group Strategies into Powerful Enantioselective Synthetic Methods", Angew. Chem. Int. Ed. 2015, 54, 9456. Yao, W.; Dou, X.; Lu, Y. "Highly Enantioselective Synthesis of 3,4-Dihydropyrans through a Phosphine-Catalyzed [4+2] Annulation of Allenones and b,g-Unsaturated a-Keto Esters", J. Am. Chem. Soc. 2015, 137, 55. (highlighted in SYNFACTS 2015, 201) Jiang, C.; Lu, Y.; Hayashi, T. "High Performance of a Palladium-Phosphinooxazoline Catalyst in Asymmetric Arylation of Cyclic N-Sulfonyl Ketimines ", Angew. Chem. Int. Ed. 2014, 53, 9936.(highlighted in SYNFACTS 2014, 1203) Han, X.; Yao, W.; Wang, T.; Tan, Y. R.; Yan, Z.; Kwistkowski, J.; Lu, Y. "Asymmetric Synthesis of Spiropyrazolones via Phosphine-Catalyzed [4+1] Annulation", Angew. Chem. Int. Ed. 2014, 53, 5643. Wang, T.; Yao, W.; Zhong, F.; Pang, G. H.; Lu, Y. "Phosphine Catalyzed Enantioselective g-Addition of 3-Substituted Oxindoles to 2,3-Butadienoates and 2-Butynoates: Use of Prochiral Nucleophiles", Angew. Chem. Int. Ed. 2014, 53, 2964.