Stanley Group | Publications

Published at Iowa State University

45. Tran, H. N.; Burgett, R. W.; Stanley, L. M. “Nickel-Catalyzed Asymmetric Hydroarylation of Vinylarenes: Direct Enantioselective Synthesis of Chiral 1,1-Diarylethanes” J. Org. Chem. 2021, 86, 3836–3849. DOI: 10.1021/acs.joc.0c02556

44. Koeritz, M. T.; Burgett, R. W.; Kadam, A. A.; Stanley, L. M. “Ni-Catalyzed Intermolecular Carboacylation of Internal Alkynes via Amide C–N Bond Activation” Org. Lett. 2020, 22, 5731–5736. DOI: 10.1021/acs.orglett.0c01607

43. Heintz, P. M.; Schumacher, B. P.; Chen, M.; Huang, W.; Stanley, L. M. “A Pd(II)-Functionalized Covalent Organic Framework for Catalytic Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones” ChemCatChem. 2019, X, XX–XX.

DOI: 10.1002/cctc.201900894

42. Kadam, A. A.; Metz, L. T.; Qian, Y.; Stanley, L. M. “Ni-Catalyzed Three-Component Alkene Carboacylation Initiated by Amide

C-N Bond Activation” Acs Catal. 2019, 9, 5651–5656. DOI: 10.1021/acscatal.9b01620

41. Metz, L. T.; Leng, M.; Evans, J.; Stanley, L. M. “Synthesis of heteroarylated ketones via bismuth(III) triflate-promoted regioselective 1,4- and 1,6-additions of electron-rich heteroarenes to cyclic enones and dienones” Tetrahedron. 2018, 26, 328-3292. DOI: 10.1016/j.tet.2018.04.002

40. Metz, L. T.; Lutovsky, A. G.; Stanley, L. M. “An Acid-Catalyzed Addition and Dehydration Sequence for the Synthesis of

Heteroarylated Steroidal Dienes” J. Org. Chem. 2018, 83, 1643–1648. DOI: 10.1021/acs.joc.7b03045

39. Fei, T.; Walker, J. A.; Vickerman, K. L.; Stanley, L. M.; Jarboe, D.; Wang, T. “Synthesis and characterization of soybean oil-based waxes and their application as paraffin substitute for corrugated coating” Ind. Eng. Chem. Res. 2018, 56, 16371–16375.

DOI: 10.1016/j.jiec.2017.09.015

38. Li, X.; Zhang, B.; Tang, L.; Tian, W. G.; Qi, S.; Volkov, A.; Pei, Y.; Qi, Z.; Tsung, C.; Stanley, L. M.; Huang, W“Cooperative

Multifunctional Catalysts for Nitrone Synthesis: Platinum Nanoclusters in Amine‐Functionalized Metal–Organic Frameworks”

Angew. Chem. Int. Ed. 2017, 58, 113–122. DOI: 10.1002/anie.201710164

37. Vickerman, K. L.; Stanley, L. M. “Catalytic, Enantioselective Synthesis of Polycyclic Nitrogen, Oxygen, and Sulfur Heterocycles

via Rh-Catalyzed Alkene Hydroacylation” Org. Lett. 2017, 19, 5054–5057. DOI: 10.1021/acs.orglett.7b02230

36. Kadam, A. A.; Ellern, A.; Stanley, L. M. “Enantioselective, Palladium-Catalyzed Conjugate Additions of Arylboronic Acids to

Form Bis-benzylic Quaternary Stereocenters” Org. Lett. 2017, 15, 4062–4065. DOI: 10.1021/acs.orglett.7b01825

35. Walker, J. A.; Vickerman, K. L.; Humke, J. N.; Stanley, L. M. “Ni-Catalyzed Alkene Carboacylation via Amide C–N Bond

Activation” J. Am. Chem. Soc. 2017, 30, 10228–10231. DOI: 10.1021/jacs.7b06191

34. Metz, T. L.; Evans, J.; Stanley, L. M. “Catalytic Conjugate Addition of Electron-Rich Heteroarenes to ß,ß-Disubstituted Enones”

Org Lett. 2017, 13, 3442-3445. DOI: 10.1021/acs.orglett.7b01402

33. Gerten, A. L.; Stanley, L. M. “Palladium-catalyzed conjugate addition of arylboronic acids to 2-substituted chromones in

aqueous media” Tetrahedron Lett. 2016, 49, 5460-5463. DOI: 10.1016/j.tetlet.2016.10.084

32. Walker, J. A.; Stanley, L. M. “N-Heterocyclic carbene-catalysed intramolecular hydroacylation to form basic nitrogen-containing heterocycles” Org. Biomol. Chem. 2016, 42, 9981-9984. DOI: 10.1039/C6OB01956K

31. Gao, M.; Cao, M.; Suastegui, M.; Walker, J. A.; Rodriguez-Quiroz, N.; Wu, Y.; Tribby, D.; Okerlund, A.; Stanley, L. M.; Shanks, J. V.; Shao, Z. “Innovating a Nonconventional Yeast Platform for Producing Shikimate as the Building Block of High-Value Aromatics” ACS Synth. Biol. 2017, 6, 29-38. DOI: 10.1021/acssynbio.6b00132

30. Johnson, K. F.; Schneider, E. A.; Schumacher, B. P.; Ellern, A.; Scanlon, J. D.; Stanley, L. M. “Rhodium-Catalyzed, Enantioselective Intramolecular Hydroacylation of Trisubstituted Alkenes” Chem. Eur. J. 2016, 44, 15619–15623.

DOI: 10.1002/chem.201603880

29. Li, X.; Van Zeeland, R.; Maligal-Ganesh, R. V.; Pei, Y.; Power, G.; Stanley, L. M.; Huang, W. “Impact of Linker Engineering on the Catalytic Activity of Metal-Organic Frameworks Containing Pd(II)-Bipydridine Complexes” ACS Catal. 2016, 6, 6324-6328.

DOI: 10.1021/acscatal.6b01753

28. Ghosh, A.; Bainbridge, D. T.; Stanley, L. M. “Enantioselective Model Synthesis and Progress toward the Putative Structure of

Yuremamine” J. Org. Chem. 2016, 81, 7945-7951. DOI: 10.1021/acs.joc.6b01730

27. Ghosh, A.; Walker Jr., J. A.; Ellern, A.; Stanley, L. M. “Coupling Catalytic Alkene Hydroacylation and α-Arylation:

Enantioselective Synthesis of Heterocyclic Ketones with α-Chiral Quaternary Sterocenters” ACS Catal. 2016, 6, 2673-2680.

DOI: 10.1021/acscatal.6b00365

26. Van Zeeland, R.; Li, X.; Huang, W.; Stanley, L. M. “MOF-253-Pd(OAc)2: A Recyclable MOF for Transition-Metal Catalysis in

Water” RSC Adv. 2016, 6, 56330-56334. DOI: 10.1039/C6RA12746K

25. Ghosh, A.; Johnson, K. F.; Vickerman, K. L.; Walker, J. A.; Stanley, L. M. “Recent Advances in Transition Metal-Catalysed

Hyroacylation of Alkenes and Alkynes” Org. Chem. Front. 2016, 3, 639-644. DOI: 10.1039/C6QO00023A

24. Gerten, A. L.; Stanley, L. M.; “Enantioselective Dearomative [3+2] Cycloadditions of Indoles with Azomethine Ylides Derived

from Alanine Imino Esters” Org. Chem. Front. 2016, 3, 339-343. DOI: 10.1039/C5QO00346F

23. Johnson, Kirsten F.; Schmidt, Adam C.; Stanley, L. M.; “Rhodium-Catalyzed, Enantioselective Hydroacylation

of ortho-Allylbenzaldehydes” Org. Lett. 2015, 50, 2765-2768. DOI: 10.1021/acs.orglett.5b02559

22. Van Zeeland, Ryan; Stanley, Levi M. “Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to ß,ß-Disubstituted

Enones in Aqueous Media: Formation of Bis-benzylic and ortho-Substituted Quaternary Centers” ACS Catal. 2015, 5,

5203-5206. DOI: 10.1021/acscatal.5b01272

21. Du, X.W.; Stanley, L. M. “Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of

2,3-Disubstituted Chroman-4-ones and Fluorinated Derviatives” Org. Lett. 2015, 17, 3276-3279.

DOI: 10.1021/acs.orglett.5b01447

20. Du, X.W.; Ghosh, A.; Stanley, L. M. “Enantioselective Synthesis of Polycyclic NitrogenHeterocycles by Rh-Catalyzed Alkene

Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance” Org. Lett. 2014, 16, 4036-4039.

DOI: 10.1021/ol501869s

19. Ghosh, A.; Stanley, L. M.; “Enantioselective hydroacylation of N-vinylindole-2-carboxaldehydes” Chem. Commun. 2014, 50,

2765-2768. DOI: 10.1039/c4cc00210e

18. Gerten, A.L.; Slade, M.C.; Pugh, K.M.; Stanley, L. M.; “Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines

with methyleneindolinones” Org. Biomol. Chem. 2013, 11, 7834-7837. DOI: 10.1039/c3ob41815d

17. Johnson, K.F.; Van Zeeland, R.; Stanley, L. M.; “Palladium-Catalyzed Synthesis of N-tert-Prenylindoles” Org. Lett. 2013, 15,

2798-2801. DOI: 10.1021/ol4011344

Prior Publications (Ph.D. / Postdoctoral)

16. Liao, X.; Stanley, L. M.; Hartwig, J. F. “Enantioselective Total Syntheses of (–)-Taiwaniaquinone H and (–)-Taiwaniaquinol B by

Iridium-Catalyzed Borylation and Palladium-Catalyzed Asymmetric Î±-Arylation” J. Am. Chem. Soc. 2011, 133, 2088-2091.

15. Stanley, L. M.; Bai, C.; Ueda, M.; Hartwig, J. F. “Iridium-Catalyzed Kinetic Asymmetric Transformations of Racemic Allylic

Benzoates” J. Am. Chem. Soc. 2010, 132, 8918-8920.

14. Sibi, M. P.; Cruz, Jr., W.; Stanley, L. M. “Enantioselective Diels-Alder Cycloadditions with beta-Substituted Pyrazolidinone

Propiolimides” Synlett 2010, 889-892.

13. Stanley, L. M.; Hartwig, J. F. “Iridium-Catalyzed Regio- and Enantioselective N-Allylation of Indoles” Angew. Chem. Int. Ed.

2009, 48, 7841-7844.

12. Pouy, M. J.; Stanley, L. M.; Hartwig, J. F. “Enantioselective, Iridium-Catalyzed Monoallylation of Ammonia” J. Am. Chem. Soc.

2009, 131, 11312-11313.

11. Stanley, L. M.; Hartwig, J. F. “Regio- and Enantioselective N-Allylations of Imidazole, Benzimidazole, and Purine Heterocycles

Catalyzed by Single-Component Metallacyclic Iridium Complexes” J. Am. Chem. Soc. 2009, 131, 8971-8983.

10. Sibi, M. P.; Kawashima, K.; Stanley, L. M. “Diels-Alder Cycloaddition Strategy for Kinetic Resolution of Chiral Pyrazolidinones”

Org. Lett. 2009, 11, 3894.

9. Sibi, M. P.; Coulomb, J.; Stanley, L. M. “Enantioselective Enolate Protonations: Friedel-Crafts Reactions with alpha-Substituted

Acrylates” Angew. Chem. Int. Ed. 2008, 47, 9913-9915.

8. Sibi, M. P.; Nie, X.; Shackleford, J. P.; Stanley, L. M.; Bouret, F. “Exo- and Enantioselective Diels-Alder Reactions: Pyrazolidinone

Auxiliaries as a Means to Enhanced Exo Selectivity” Synlett 2008, 2655-2658.

7. Sibi, M. P.; Rane, D.; Stanley, L. M.; Soeta, T. “Copper(II)-Catalyzed Exo and Enantioselective Cycloadditions of Azomethine

Imines” Org. Lett. 2008, 10, 2971-2974.

6. Sibi, M. P.; Stanley, L. M.; Soeta, T. “Enantioselective 1,3-Dipolar Cycloadditions of Diazoacetates with Electron-Deficient

Olefins” Org. Lett. 2007, 9, 1553-1556.

5. Sibi, M. P.; Chen, J.; Stanley, L. “Enantioselective Diels-Alder Reactions. Effect of the Achiral Template on Reactivity and

Selectivity” Synlett 2007, 298-302.

4. Sibi, M. P.; Stanley, L. M.; Nie, X.; Venkatraman, L; Liu, M.; Jasperse, C. P. “The Role of Achiral Pyrazolidinone Templates in

Enantioselective Diels-Alder Reactions: Scope, Limitations, and Conformational Insights” J. Am. Chem. Soc. 2007, 129, 395-

405.

3. Sibi, M. P.; Stanley, L. M.; Soeta, T. “Enantioselective 1,3-Dipolar Cycloaddition of Nitrile Imines to alpha-Substituted and

alpha,beta-Disubstituted, alpha,beta-Unsaturated Carbonyl Substrates: A Method for Synthesizing Dihydropyrazoles

Bearing a Chiral Quaternary Center” Adv. Synth. Catal. 2006, 348, 2371-2375.

2. Sibi, M. P.; Stanley, L. M.; Jasperse, C. P. “An Entry to a Chiral Dihydropyrazole Scaffold: Enantioselective [3+2] Cycloaddition of

Nitrile Imines” J. Am. Chem. Soc. 2005, 127, 8276-8277.

-Highlighted in Chemistry and Industry: Burgess, K. Chemistry and Industry 2005, 19 September 2005 - Issue No 18, 32.

-Highlighted in the News and View Section of Letters in Organic Chemistry. Letters in Organic Chemistry 2006, 3 78-81.

1. Sibi, M. P.; Stanley, L. M. “Enantioselective Diethylzinc Additions to Aldehydes Catalyzed by Chiral Relay Ligands” Tetrahedron:

Asymmetry 2004, 15, 335-3356.

Book Chapters, Book Contributions, and Review Articles

6. Stanley, L. M.; Sibi, M. P. “Chiral Bisoxazoline Ligands” In Privileged Chiral Ligands and Catalysts; Zhou, Q.-L., Ed.; Wiley-VCH,

Weinheim, Germany, 2011, pp. 171-220.

5. Hartwig, J. F.; Stanley, L. M. “Mechanistically Driven Development of Iridium Catalysts for Asymmetric Allylic Substitution” Acc.

Chem. Res. 2010, 43, 1461-1475.

4. Stanley, L. M.; Hartwig, J. F. “Copper-Catalyzed Allylic Substitution” In Organotransition Metal Chemistry: From Bonding to

Catalysis; Hartwig, J. F., Ed.; University Science Books, Sausalito, CA, 2010, pp. 999-1008.

3. Stanley, L. M.; Sibi, M. P. “Enantioselective Copper-Catalyzed 1,3-Dipolar Cycloadditions” Chem. Rev. 2008, 108, 2887-2902.

2. Stanley, L. M.; Sibi, M. P. “Cu(I) and Cu(II) Lewis Acids” In Acid Catalysis in Modern Organic Synthesis; Yammamoto, H.;

Ishihara, K., Eds.; Wiley-VCH, Weinheim, 2008, Vol. 2, pp. 903-985.

1. Stanley, L. M.; Sibi, M. P. “5,5-Dimethyl-1-(phenylmethyl)-3-pyrazolidinone” Encyclopedia of Reagents for Organic Synthesis

(e-EROS) 2006.

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