Scheidt Group Publications

updated 10/8/09

     
76 Phillips, E. M.; Chan, A.; Scheidt, K. A. “Discovering New Reactions with N-Heterocyclic Carbene Catalysis,” Aldrichimica Acta, 2009, in press.  
75 Nibbs, A. E.; Maize, A. L.; Herter, R. M.; Scheidt, K. A. “Catalytic Asymmetric Alkylation of Substituted Isoflavanones,” Org. Lett. 2009, 11, 4010-4013
74 Lee, J. Y.; Roberts, J. M.; Farha, O. K.; Sarjeant, A. A.; Scheidt, K. A.; Hupp, J. T. “Synthesis and Gas Sorption Properties of a Metal-Azolium Framework Material,” Inorganic Chemistry, 2009, ASAP.
73 Maki, B. E.; Patterson, E. V.; Cramer, C. J.; Scheidt, K. A. “The Impact of Solvent Polarity on N-Heterocyclic Carbene-Catalyzed b-Protonations of Homoenolate Equivalents,” Org. Lett. 2009, 11, 3942-3945.
72 Custar, D. W.; Zabawa, T. P.; Hines, J.; Crews, C.; Scheidt, K. A. “Total Synthesis and Biological Investigation of Neopeltolide Leading to a Structural Reassignment and Analog Evaluations,” J. Am. Chem. Soc. 2009, 131, 12406-12414.
71 Lettan II, R. B.; Galliford, C. V.; Woodward, C. C.; Scheidt, K. A. “Amide Enolate Additions to Acylsilanes:  In situ Generation of Unusual and Stereoselective Homoenolate Equivalents,” J. Am. Chem. Soc. 2009, 131, 8805-8814.
70 Lee, J. Y.; Farha, O.; Roberts, J. T; Scheidt, K. A.; Nguyen, S. T.; Hupp, J. T. “The Metal Organic Framework as a Catalyst,” Chem. Soc. Rev. 2009, 38, 1450-1459.
69 Xu, L.; Ding, Y.; Catalona, W. J.; Yang, X.; Anderson, W. F.; Jovanovic, B.; Wellman, K.; Scheidt, K. A.; Kilmer, J.; Cooper, J.; Montgomery, R. B.; Bergan, R. C. “MEK4 is identified as an important regulator of human prostate cell motility and therapeutic target,” J. Nat. Can. Inst. 2009, 101, 1141-1155
68 Maki, B. E.; Scheidt, K. A. “Single-Flask Synthesis of N-Acylated Indoles by Catalytic Dehydrogenative Coupling with Primary Alcohols,” Org. Lett. 2009, 11, 1651-1654.
67 Phillips, E. M.; Wadamoto, M.; Roth, H. S.; Scheidt, K. A. “N-Heterocyclic Carbene-Catalyzed Michael Reactions of Aryloxyaldehydes,” Org. Lett. 2009, 11, 105-108.
66 Reynolds, T. E.; Binkely, M. S.;Scheidt, K. A. “Highly Selective α-Acylvinyl Anion Additions to Imines,” Org. Lett. 2009, 10, 5227-5230.
65 Mathies, A. K.; Mattson, A. E.; Scheidt, K. A. “Intermolecular Crossed-Acyloin Reactions by Fluoride-Promoted Additions of O-Silyl Thiazolium Carbinols,” Synthesis, Invited Contribution to Special Edition For Journal Awardees. 2009, 377-383.
64 Phillips, E. M.; Wadamoto, M.; Scheidt, K. A. “N-Heterocyclic Carbene-Catalyzed Desymmetrizations,” Synthesis, 2009, Invited PSP article, 687-690.
63

Maki, B. E.; Chan, A.; Phillips, E. M.; Scheidt, K. A. “N-Heterocyclic Carbene-Catalyzed Oxidations” Tetrahedron, invited article for special Justin DuBois Issue. 2009, 65, 3102-3109.
62 Gibbs-Davis, J. M.; Kruk, J. J.; Konek, C. T.; Scheidt, K. A.; Geiger, F. M. “Jammed Acid-Base Reactions at Interfaces,” J. Am. Chem. Soc. 2008, 130, 15444-15447.
61 Stokes, G. Y.; Buchbinder, A. M.; Gibbs-Davis, J. M.; Scheidt, K. A.; Geiger, F. M. “Heterogeneous Ozone Oxidation Reactions of 1-Pentene, Cyclopentene, Cyclohexene, and a Menthenol Derivative Studied by Sum Frequency Generation,” J. Phys. Chem. A. 2008, 112, 11688-11698.
60 Maki, B. E. and Scheidt, K. A. "N-Heterocyclic Carbene-Catalyzed Oxidation of Unactivated Aldehydes to Esters," Org. Lett. 2008, 10, 4331-4334.
59

Reynolds, T. E.; Binkley, M. S.; Scheidt, K. A. “Lewis Acid-Catalyzed Conjugate Additions of Silyloxyallenes: A Selective Solution to the Intermolecular Rauhut−Currier Problem” Org. Lett., 2008, 10, 2449–2452.
58

Maki, B. E.; Chan. A.; Scheidt, K. A. “Protonation of Homoenolate Equivalents Generated by N-Heterocyclic Carbenes” Synthesis, invited Feature Article. 2008, 1306-1315.
57

Galliford, C. V. and Scheidt, K. A. "An Unusual Dianion Equivalent from Acylsilanes for the Synthesis of Substituted b-Keto Esters," Chem. Comm. 2008, 1926-1928.
56

Chan. A. and Scheidt, K. A. “Direct Umpolung Amination of Homoenolates Catalyzed by N-Heterocyclic Carbenes,” J. Am. Chem. Soc. 2008, 130, 2740-2741.
55

Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. “Enantioselective Homoenolate Additions to Nitrones Catalyzed by N-Heterocyclic Carbenes,” J. Am. Chem. Soc. 2008, 130, 2416-2417.
54

Lettan II, R. B.; Woodward, C. C.; Scheidt, K. A. “Stereoselective Synthesis of Highly Substituted g-Lactams From Acylsilanes,” Angew. Chem. Int. Ed. 2008, 47, 2294-2297.
53

Custar, D. W.; Zabawa, T. P.; Scheidt, K. A. “Total Synthesis and Structural Revision of the Marine Macrolide Neopeltolide,” J. Am. Chem. Soc. 2008, 130, 804-805. C&E News magazine write up about neopeltolide here.
52

Dieringer, J. A.; Lettan, R. B., II; Scheidt, K. A.; Van Duyne, R. P. “Isotope Labeled Single Molecule Surface-Enhanced Raman Spectroscopy: Existence Proof and Dynamics,” J. Am. Chem. Soc. 2007, 129, 16249-16256.
51

Reynolds, T. E.; Scheidt, K. A. “Catalytic Enantioselective a-Acylvinyl Addition Reactions of Silyloxyallenes,” Angew. Chem Int. Ed. 2007, 46, 7806-7809.

50

Wadamoto, M.; Phillips, E.M.; Reynolds, T. E.; Scheidt, K. A. “Enantioselective Synthesis of a,a-Disubstituted Cyclopentenes by N-Heterocyclic Carbene-Catalyzed Desymmetrization of 1,3-Diketones,” J. Am. Chem. Soc. 2007, 129, 10098-10099.
49

Scheidt, K. A. and Mattson, A. E.  “5-(1,1-dimethylethyl)-5,6-dihydro-2-phenyl-(5S)-oxazolo[2,3-c]-1,2,4-triazolium tetrafluoroborate.” in The Electronic Encyclopedia of Reagents for Organic Synthesis. 2007.

48

Reynolds, T. E.; Stern, C.; Scheidt, K. A. “N-Heterocyclic Carbene-Initiated a-Acylvinyl Anion Reactivity: Additions of a-Hydroxy-propargylsilanes to Aldehydes,” Org. Lett. 2007, 9, 2581-2584.
47

Galliford, C. V.; Scheidt, K. A. “Pyrrolidinyl-Spirooxindole Natural Products as Inspirations for the Development of Therapeutic Agents,“ Angew. Chem. Int. Ed. 2007, 46, 8748-8758.
46

Chan, A.; Scheidt, K. A. “Highly Stereoselective Formal [3+3] Cycloaddition of Enals and Azomethine Imines Catalyzed by N-Heterocyclic Carbenes,” J. Am. Chem. Soc. 2007, 129, 5334-5335.

45

Gibbs-Davis, J. M.; Hayes, P. L.; Scheidt, K. A.; Geiger, F. M. “Anion Chelation by Amino Acid-Functionalized Fused Quartz/Water Interfaces Studied by Nonlinear Optics,” J. Am. Chem. Soc. 2007, 129, 7175-7184.
44

Milgram, B. C.; Eskildsen, K.; Richter, S. M.; Scheidt, W. R., Scheidt, K. A. “Microwave-Assisted Piloty–Robinson Synthesis of 3,4-Disubstitued Pyrroles,” J. Org. Chem. 2007, 72, 3941-3944.
43

Mattson, A. E.; Scheidt, K. A. “Nucleophilic Acylation of Quinone Methides:  An Umpolung Strategy for the Synthesis of a-Aryl Ketones and Benzofurans,” J. Am. Chem. Soc. 2007, 129, 4508-4509.
42

Biddle, M. A.; Lin, M.; Scheidt, K. A. “Enantioselective Catalytic Synthesis of Flavanones and Chromanones” J. Am. Chem. Soc. 2007, 129, 3830-3831.
41

Phillips, E. M.; Wadamoto, M.; Chan, A.; Scheidt, K. A. “Highly Enantioselective Intramolecular Michael Additions Catalyzed by N-Heterocyclic Carbenes,” Angew. Chem. Int. Ed. 2007, 46, 3107-3110.

40

Galliford, C. V.; Scheidt, K. A. "Catalytic Multicomponent Reactions for the Synthesis of N-Aryl Trisubstituted Pyrroles," J. Org. Chem. 2007, 72, 1811-1813.
39

Hayes, P. L.; Gibbs-Davis, J. M.; Musorrafiti, M. J.; Mifflin,A. M.; Scheidt, K. A.; Geiger, F. M. “Environmental Biogeochemistry Studied by Second Harmonic Generation: A Look at the Agricultural Antibiotic Oxytetracycline,”  invited contribution to the Kenneth B. Eisenthal Festschrift in for J. Phys. Chem. C. 2007, 111, 8796-8804.

38

Maki, B. E.; Chan, A.; Phillips, E. M.; Scheidt, K. A. “Tandem Oxidation of Allylic and Benzylic Alcohols to Esters Catalyzed by N-Heterocyclic Carbenes,” Org. Lett. 2007, 9, 371-374.

37

Lettan II, R. B.; Milgram, B. C.; Clark, C. T.; Scheidt, K. A. “Synthesis of Acylsilanes from Morpholine Amides. Synthesis of 1-(Dimethyl(Phenyl)silylpropan-1-one,” Org. Syn. 2007, 84, 22.
36

Voges. A.B; Yin, G.; Gibbs Davis, J.; Lettan, R. B., II; Bertin, P. A.; Pike, R. C.; Nguyen, S. T.; Scheidt, K. A.; Geiger, F. M. “Synthesis, Characterization and Reaction of Terpenes Relevant to Heterogeneous Tropospheric Chemistry,” J. Phys. Chem. C. Feature article. 2007, 111, 1567-1578.

35

Galliford, C. V.; Martenson, J. S.; Stern, C. A.; Scheidt, K. A. “A Highly Diastereoselective, Catalytic Multicomponent Assembly Reaction for the Synthesis of Spiropyrrolidinyloxindoles,” Chem. Commun. 2007, 631-633.
34

Lettan II, R. B.; Reyonlds, T. E.; Galliford, C. V.; Scheidt, K. A. “Synthesis of Tertiary b-Hydroxy Amides by Enolate Additions to Acylsilanes,” J. Am. Chem. Soc. 2006, 128, 15566-15567.
33

‘Triethoxysilane (Update).’ Scheidt, K. A. and Lettan II, R. B. in ‘The Electronic Encyclopedia of Reagents for Organic Synthesis’. 2006-2007.
32

Reynolds, T. E.; Bharadwaj, A. R.; Scheidt, K. A. “Stereoselective Lewis Acid-Catalyzed a-Acylvinyl Additions,” J. Am. Chem. Soc. 2006, 128, 15382-15383.

31

Mattson, A. E.; Bharadwaj, A. R.; Zuhl, A. M.; Scheidt, K. A. "Thiazolium-Catalyzed Additions of Acylsilanes: A General Strategy for Acyl Anion Addition Reactions," J. Org. Chem. 2006, 71, 5715-5724.

30

Chan, A.; Scheidt, K. A. “Hydroacylation of Activated Ketones Catalyzed by N-Heterocyclic Carbenes,” J. Am. Chem. Soc. 2006, 128, 4558-4559.
29

Mattson, A. E.; Zuhl, A. M.; Reynolds, T. E.; Scheidt, K. A. “Direct Nucleophilic Acylation of Nitroalkenes Using Thiazolium Carbinols Promoted by a Thiourea/Fluoride Anion Combination,” J. Am. Chem. Soc. 2006, 128, 4932-4933.
28

Graves, C. R.; Scheidt, K. A.; Nguyen, S. T. “Practical Enantioselective MSPV Reduction of Ketimines Using (BINOL)AlIII” Org. Lett. 2006, 8, 1229-1232

27

Myers, M. C.; Bharadwaj, A. R; Milgram, B. C.; Scheidt, K. A. "Catalytic Conjugate Additions of Carbonyl Anions under Neutral Aqueous Conditions,” J. Am. Chem. Soc. 2005, 127, 14675-14680.
26

Lettan, R. B., II; Scheidt, K. A. “Lewis Base-Catalyzed Additions of Trialkoxysilylalkynes to Carbonyl Compounds,” Org. Lett. 2005, 7, 3227-3230.

25

Ballweg, D.M.; Miler, R. C.; Grey, D. L; Scheidt, K. A. "Stereoselective Synthesis of a-Silylamines by the Direct Addition of Silyl Anions to Actived Imines” Org. Lett. 2005, 7, 1403-1406.
24

Morris, W. J.; Custar, D. W.; Scheidt, K. A. “Stereoselective Synthesis of Tetrahydropyran-4-ones via a One-Pot Scandium(III) Triflate-Catalyzed Cyclization/Ring-Opening Strategy,” Org. Lett. 2005, 7, 1113-1116.
23

Chernick, E. T.; Ahrens, M. J.; Scheidt, K. A.; Wasielewski, M. R. "Copper-Promoted N-Arylation of Cyclic Imides for the Synthesis of Extended Aromatic Systems,” J. Org. Chem.2005, 70, 1486-1489.

22

Chan, A.; Scheidt, K. A. " Conversion of a,b-Unsaturated Aldehydes into Saturated Esters: An Umpolung Reaction Catalyzed by Nucleophilic Carbenes,” Org. Lett. 2005. 7, 905-908.
21

Mattson, A. E.; Scheidt, K. A. "Catalytic Additions of Acylsilanes to Imines: An Acyl Anion Strategy for the Direct Synthesis of -Amino Ketones," Org. Lett. 2004, 6, 4363-4366.
20

Clark, C. T.; Milgram, B. C.; Scheidt, K. A. "Efficient Synthesis of Alkyl Acylsilanes from Morpholine Amides," Org. Lett. 2004, 6, 3977-3980.
19

Bharadwaj, A. R.; Scheidt, K. A. "Catalytic Multicomponent Synthesis of Highly Substituted Pyrroles Utilizing a One-Pot Sila-Stetter/Paal–Knorr Strategy," Org. Lett. 2004, 6, 2465-2468.
18

Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. "The Thiazolium-Catalyzed Sila-Stetter Reaction: Conjugate Addition of Acylsilanes to Unsaturated Esters and Ketones," J. Am . Chem. Soc. 2004, 126, 2314-2315.

17

Clark, C. T.; Lake, J. F.; Scheidt, K. A. "Catalytic Disilylation of Alkylidene Malonates Employing a Lewis Base Activation Strategy," J. Am. Chem. Soc. 2004, 126, 84-85.
16

Galliford, C. V; Beenen, M. A.; Nguyen, S. T.; Scheidt, K. A.; “Catalytic, Three-Component Assembly Reaction for the Synthesis of Pyrrolidines,” Org. Lett. 2003, 5, 3487-3490.
Publications as Postdoctoral Fellow and Graduate Student
15 Handa, M.; Scheidt, K. A.; Bossart, M.; Zheng, N.; Roush, W. R. “Studies on the Synthesis of Apoptolidin A. 1. Synthesis of the C(1)-C(11) Fragment,” J. Org. Chem. 2008, 73, 1031-1035.
14 Evans, D. A; Fandrick, K. R.; Song, H.-J.; Scheidt, K. A.; Xu, R. “Enantioselective Friedel-Crafts Alkylations Catalyzed by Bis(oxazolinyl)pyridine-Scandium Triflate Complexes,” J. Am. Chem. Soc. 2007, 129, 10029-10041.
13 Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. "Enantioselective Indole Friedel Crafts Alkylations Catalyzed by Bis(oxazolinyl)pyridine-Scandium(III) Triflate Complexes," J. Am. Chem. Soc. 2003, 125, 10780-10781.
12 Evans, D. A.; Borg, G.; Scheidt, K. A. "Stable Tetrahedral Intermediates-Carbinols from Acyl Pyrroles," Angew. Chem., Int. Ed. Engl. 2002, 41, 3189-3191.
11 Scheidt, K. A.; Bannister, T. D.; Tasaka, A.; Wendt, M. D.; Savall, B. D.; Fegley, G. J.; Roush, W. R. "Total Synthesis of (-)-Bafilomycin A1," J. Am. Chem. Soc. 2002, 124, 6981-6990.
10 Roush, W. R.; Bannister, T. D.; Wendt, M. D.; Jablonowski, J. A.; Scheidt, K. A. "Studies on the Synthesis of Bafilomycin A: Stereochemical Aspects of the Fragment Assembly Aldol Reaction for Construction of the C(13)-C(25) Segment," J. Org. Chem. 2002, 67, 4275-4283.
9 Roush, W. R.; Bannister, T. D.; Wendt, M. D.; VanNieuwenhze, M. S.; Gustin, D. J.; Dilley, G. D.; Lane, G. C.; Scheidt, K. A.; Smith, W. J. "An NMR Method for Assigning Stereochemistry to Hydroxy Ketones Deriving from Aldol Reactions of Methyl Ketones," J. Org. Chem. 2002, 67, 4284-4289.
8 Evans, D. A.; Scheidt, K. A.; Downey, C. W. "Synthesis of (-)-Epibatidine," Org. Lett. 2001, 3, 3009-3012.
7 Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. "Enantioselective and Diastereoselective Mukaiyama Michael Reactions Catalyzed by Bis(oxazoline) Copper(II) Complexes," J. Am. Chem. Soc. 2001, 123, 4480-4491.
6 Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. "Total Synthesis of Bafilomycin A: Application of Diastereoselective Crotylboration and Methyl Ketone Aldol Reactions," Angew. Chem., Int. Ed. Eng. 1999, 38, 1652-1655.
5 Scheidt, K. A.; Roush, W. R.; McKerrow, J. H.; Selzer, P. M.; Hansell, E. "Design, Synthesis and Evaluation of Conformationally Constrained Cysteine Protease Inhibitors," Bioorg. Med. Chem. 1998, 6, 2477-2494.  
4 Roush, W. R.; Gwaltney, S. L.; Cheng, J.; Scheidt, K. A.; McKerrow, J. H.; Hansell, E. "Vinylsulfonates and Vinylsulfonamides: Potent, Irreversible Inhibitors of Cysteine Proteases," J. Am. Chem. Soc. 1998, 120, 10994-10995.
3 Scheidt, K. A.; Chen, H.; Follows, B. C.; Chemler, S. R.; Coffey, D. S.; Roush, W. R. "Tris(dimethylamino)sulfonium difluorotrimethylsilicate, a Mild Reagent for the Removal of Silicon Protecting Groups," J. Org. Chem. 1998, 63, 6436-6437.
2 Scheidt, K. A.; Roush, W. R. "Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis: Enantioselective Synthesis of Sch 38516 (Fluvirucin B)," Chemtracts 1998, 11, 522-530.  
1 Miller, M. J.; Darwish, I.; Ghosh, A.; Ghosh, M.; Hansel, J.-G.; Hu, J.; Niu, C.; Ritter, A.; Scheidt, K. A.; Süling, C.; Sun, S.; Zhang, D.; Buddle, A.; De Clercq, E.; Long, S.; Malouin, F.; Moellmannin, U. "Design, Syntheses and Studies of New Antibacterial, Antifungal and Antiviral Agents," Anti-infectives: Recent Advances in Chemistry and Structure-Activity Relationships. P. H. Bentley and P. J. O'Hanlon, Eds. Royal Society of Chemistry Special Publication No. 198. Cambridge, UK. 1997.