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Pu, Lin

Lin Pu

Primary Appointment

Chemistry

Contact Information

Email: lp6n@virginia.edu

Research Interests

Multi-disciplinary research programs involving organic synthesis, polymer chemistry, dendrimers, organometalic chemistry, asymmetric catalysis, and molecular recognition

Research Description

Multi-disciplinary research programs involving organic synthesis, asymmetric catalysis, molecular recognition, fluorescent sensors and polymers are conducted in our laboratory. The 1,1?-bi-2-naphthol and its derivatives are chosen as the chiral building blocks to construct novel chiral molecules and macromolecules for diverse applications. We have discovered that the Lewis acid complexes of the optically active binaphthyl molecules and polymers can carry out highly enantioselective organic reactions such as organozinc additions to aldehydes, hetero-Diels-Alder reactions, 1,3-dipolar cycloadditions, reductions of ketones, Michael additions, epoxidations and others. Interesting chiral organic molecules are prepared by using these catalysts and the biological functions of these molecules are explored through collaboration. We have developed a family of enantioselective fluorescent sensors for the recognition of organic molecules such as alpha-hydroxycarboxylic acids, amino acids, amino alcohols and amines. These sensors are potentially useful for rapid assay of the enantiomeric composition of chiral compounds and for high throughput chiral catalyst screening. The application of these sensors in biological analysis will be explored. New chiral conjugated polymers and dendrimers are also prepared for applications in materials, catalysis and sensing. New catalysts are also under development for stereocontrolled polymerization.

Selected Publications

Wen K, Yu S, Huang Z, Chen L, Xiao M, Yu X, Pu L, Rational design of a fluorescent sensor to simultaneously determine both the enantiomeric composition and the concentration of chiral functional amines., 2015; Journal of the American Chemical Society. 137(13) 4517-24 PMID: 25790271 |

Ying J, Brown KB, Sandridge MJ, Hering BA, Sabat M, Pu L, Rh(I)-catalyzed chemo- and stereoselective domino cycloaddition of optically active propargyl 2,4-hexadienyl ethers., 2015; The Journal of organic chemistry. 80(6) 3195-202 PMID: 25700088 |

Wang C, Wu E, Wu X, Xu X, Zhang G, Pu L, Enantioselective fluorescent recognition in the fluorous phase: enhanced reactivity and expanded chiral recognition., 2015; Journal of the American Chemical Society. 137(11) 3747-50 PMID: 25761050 |

Pu L, Asymmetric functional organozinc additions to aldehydes catalyzed by 1,1'-bi-2-naphthols (BINOLs)., 2014; Accounts of chemical research. 47(5) 1523-35 PMID: 24738985 | PMCID: PMC4033666

Ying J, Pu L, A facile asymmetric approach to the multicyclic core structure of mangicol A., 2014; Chemistry (Weinheim an der Bergstrasse, Germany). 20(49) 16301-7 PMID: 25302742 |

Yu S, Plunkett W, Kim M, Wu E, Sabat M, Pu L, Molecular recognition of aliphatic diamines by 3,3'-di(trifluoroacetyl)-1,1'-bi-2-naphthol., 2013; The Journal of organic chemistry. 78(24) 12671-80 PMID: 24283254 |

Yu S, Plunkett W, Kim M, Pu L, Simultaneous determination of both the enantiomeric composition and concentration of a chiral substrate with one fluorescent sensor., 2012; Journal of the American Chemical Society. 134(50) 20282-5 PMID: 23214478 |

Pu L, Enantioselective fluorescent sensors: a tale of BINOL., 2011; Accounts of chemical research. 45(2) 150-63 PMID: 21834528 |

Turlington M, Pu L, Reverse the diastereoselectivity of the Rh(I)-catalyzed Pauson-Khand cycloaddition., 2011; Organic letters. 13(16) 4332-5 PMID: 21766800 |

Turlington M, Du Y, Ostrum SG, Santosh V, Wren K, Lin T, Sabat M, Pu L, From highly enantioselective catalytic reaction of 1,3-diynes with aldehydes to facile asymmetric synthesis of polycyclic compounds., 2011; Journal of the American Chemical Society. 133(30) 11780-94 PMID: 21688803 |

Yu S, DeBerardinis AM, Turlington M, Pu L, Study of the fluorescent properties of partially hydrogenated 1,1'-bi-2-naphthol-amine molecules and their use for enantioselective fluorescent recognition., 2011; The Journal of organic chemistry. 76(8) 2814-9 PMID: 21405012 |

DeBerardinis AM, Turlington M, Pu L, Activation of vinyl iodides for the highly enantioselective addition to aldehydes., 2011; Angewandte Chemie (International ed. in English). 50(10) 2368-70 PMID: 21351356 |

Yu S, Pu L, Pseudoenantiomeric fluorescent sensors in a chiral assay., 2010; Journal of the American Chemical Society. 132(50) 17698-700 PMID: 21121601 |

Turlington M, Yue Y, Yu XQ, Pu L, Catalytic asymmetric synthesis of chiral propargylic alcohols for the intramolecular Pauson-Khand cycloaddition., 2010; The Journal of organic chemistry. 75(20) 6941-52 PMID: 20843029 |

DeBerardinis AM, Turlington M, Ko J, Sole L, Pu L, Facile synthesis of a family of H8BINOL-amine compounds and catalytic asymmetric arylzinc addition to aldehydes., 2010; The Journal of organic chemistry. 75(9) 2836-50 PMID: 20377255 |

Turlington M, DeBerardinis AM, Pu L, Highly enantioselective catalytic alkyl propiolate addition to aliphatic aldehydes., 2009; Organic letters. 11(11) 2441-4 PMID: 19422198 |

Yue Y, Yu XQ, Pu L, Base-catalyzed highly stereoselective conversion of gamma-hydroxy-alpha,beta-acetylenic esters to gamma-acetoxy dienoates., 2009; Chemistry (Weinheim an der Bergstrasse, Germany). 15(20) 5104-7 PMID: 19322771 |

Zhou LH, Yu XQ, Pu L, Reactivity of gamma-hydroxy-alpha,beta-acetylenic esters with amines: facile synthesis of the optically active 4-amino-2(5H)-furanones., 2009; The Journal of organic chemistry. 74(5) 2013-7 PMID: 19195982 |

Yue Y, Turlington M, Yu XQ, Pu L, 3,3'-Anisyl-substituted BINOL, H(4)BINOL, and H(8)BINOL ligands: asymmetric synthesis of diverse propargylic alcohols and their ring-closing metathesis to chiral cycloalkenes., 2009; The Journal of organic chemistry. 74(22) 8681-9 PMID: 19860396 |

Hyacinth M, Chruszcz M, Lee KS, Sabat M, Gao G, Pu L, Supramolecular assemblies of chiral propargylic alcohols., 2006; Angewandte Chemie (International ed. in English). 45(32) 5358-60 PMID: 16847852 |

Qin YC, Pu L, Highly enantioselective addition of diphenylzinc to aliphatic and aromatic aldehydes catalyzed by a readily available H8-binol derivative., 2005; Angewandte Chemie (International ed. in English). 45(2) 273-7 PMID: 16315332 |

Li ZB, Lin J, Pu L, A cyclohexyl-1,2-diamine-derived bis(binaphthyl) macrocycle: enhanced sensitivity and enantioselectivity in the fluorescent recognition of mandelic acid., 2005; Angewandte Chemie (International ed. in English). 44(11) 1690-3 PMID: 15688352 |

Gao G, Xie RG, Pu L, Highly enantioselective alkyne additions to aldehydes in the presence of 1,1'-bi-2-naphthol and hexamethylphosphoramide., 2004; Proceedings of the National Academy of Sciences of the United States of America. 101(15) 5417-20 PMID: 15026570 | PMCID: PMC397396

Pu L, Fluorescence of organic molecules in chiral recognition., 2004; Chemical reviews. 104(3) 1687-716 PMID: 15008630 |

Xu MH, Lin J, Hu QS, Pu L, Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching., 2002; Journal of the American Chemical Society. 124(47) 14239-46 PMID: 12440923 |

Lin J, Hu QS, Xu MH, Pu L, A practical enantioselective fluorescent sensor for mandelic acid., 2002; Journal of the American Chemical Society. 124(10) 2088-9 PMID: 11878942 |

Pu L, 1,1'-Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New Materials., 2002; Chemical reviews. 98(7) 2405-2494 PMID: 11848968 |

Pu L, Yu HB, Catalytic asymmetric organozinc additions to carbonyl compounds., 2001; Chemical reviews. 101(3) 757-824 PMID: 11712502 |

Pugh VJ, Hu QS, Pu L, The First Dendrimer-Based Enantioselective Fluorescent Sensor for the Recognition of Chiral Amino Alcohols The support of this work by the National Institute of Health (1R01GM58454) is gratefully acknowledged. We also thank the partial support from the donors of the Petroleum Research Fund-administered by the American Chemical Society., 2000; Angewandte Chemie (International ed. in English). 39(20) 3638-3641 PMID: 11091423 |