45. “Studies Toward Improved Enantiocontrol in the Asymmetric Cu-Catalyzed Reductive Coupling of Ketones and Allenamides: 1,2-Aminoalcohol Synthesis.” Collins, S.; Sieber, J. D. Org. Lett. 2023, 25, 1425 – 1430.
A preprint of this manuscript was uploaded to ChemRxiv: View
44. “Asymmetric Access to Boryl-Substituted Vicinal Aminoalcohols through Cu-Catalyzed Reductive Coupling.” Gargaro, S. L.; Sieber, J. D. ChemRxiv 2022, DOI: 10.26434/chemrxiv-2022-lmpk8
43. “Development of a Scalable Asymmetric Process for the Synthesis of GlyT1 Inhibitor BI 425809 (Iclepertin).”
Frutos, R.; Tampone, T. G.; Mulder, J.; Gao, J.; Sieber, J. D.; Rodriguez, S.; Haddad, N.; Baer, K.; Brown, J.; Yang, B. -S.; Giovannini, R.; Song, J. J.; Grinberg, N.; Lee, H.; Senanayake, C. H. Org. Process Res. Dev. 2023, DOI: doi.org/10.1021/acs.oprd.2c00373.
In phase III trials for schizophrenia (CNS): clinical trial NCT04860830 (June 18, 2021 – May 3, 2024)
42. “Asymmetric Synthesis of Propargylic alfa-Stereogenic Tertiary Amines by Reductive Alkynylation of Tertiary Amides Using Ir/Cu Tandem Catalysis.” Agrawal, T.; Perez-Morales, K. K.; Cort, J. A.; Sieber, J. D. J. Org. Chem. 2022, 87, 6387 – 6392.
A preprint of this manuscript was uploaded to ChemRxiv: View
41. “Development of a Practical Synthesis of the 8-FDC Fragment of OPC-167832.” Gopalsamuthiram, V.; Ho, D. B.; Peck C. L.; Natarajan, V.; Agrawal, T.; Burns, J.; Bachert, J.; Cook, D. W.; Stringham, R. W.; Nelson, R.; Ahmad, S.; Gupton, B. F.; Snead, D. R.; McQuade, D. T.; Vaidyanathan, R.; Donsbach, K.; Sieber, J. D. ACS Omega 2022, 7, 7223 – 7228.
A preprint of this manuscript was uploaded to ChemRxiv: View
40. “Development of a Modified System to Provide Improved Diastereocontrol in the Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenamides.” Ho, D. B.; Gargaro, S. L.; Klake, R. K.; Sieber, J. D. J. Org. Chem. 2022, 87, 2142 – 2153.
Invited contribution to the Excellence in Industrial Organic Synthesis 2021 special issue.
A preprint of this manuscript was uploaded to ChemRxiv: View
39. “Synthesis of 1,2-Aminoalcohols through Enantioselective Aminoallylation of Ketones by Cu-Catalyzed Reductive Coupling.” Klake, R. K.; Edwards, M. D.; Sieber, J. D. Org. Lett. 2021, 23, 6444 – 6449.
38. “Access to chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.” Agrawal, T.; Martin, R. T.; Collins, S.; Wilhelm, Z.; Edwards, M. D.; Gutierrez, O.; Sieber, J. D. J. Org. Chem. 2021, 86, 5026 – 5046.
37. “Cross-Coupling of Allenamides and C-Based Nucleophiles by Pd-Catalyzed Allylic Alkylation.”
Sieber, J. D.; Klake, R. K.; Agrawal, T.; Ho, D. B.; Gargaro, S. L.; Collins, S.; Edwards, M. D. Isr. J. Chem. 2021, 61, 332 – 339.
Invited special issue contribution in honor of Prof. Barry Trost’s 80th birthday.
36. “Expanding Access to Remdesivir via an Improved Pyrrolotriazine Synthesis: Supply Centered Synthesis.”
Paymode, D. J.; Cardoso, F. S. P.; Agrawal, T.; Tomlin, J. W.; Cook, D. W.; Burns, J. M.; Stringham, R. W.; Sieber, J. D.; Gupton, B. F.; Snead, D. R. Org. Lett. 2020, 22, 7656 – 7661.
35. “Identification of a Surprising Boronic Acid Homocoupling Process in Suzuki-Miyaura Cross-Coupling Reactions Utilizing a Hindered Fluorinated Arene.”
Gargaro, S. L.; Dunson, B.; Sieber, J. D. Synlett 2021, 32, 511 – 516.
Invited special issue contribution to “The Power of Transition Metals: an Unending Well-Spring of New Reactivity” celebrating the career of Prof. Barry Trost and 20 years of Science and Synthesis.
34. Invited review article: “Recent Developments in C-C Bond Formation Using Catalytic Reductive Coupling Strategies.”
Agrawal, T.; Sieber, J. D. Synthesis 2020, 52, 2623 – 2638.
33. “Access to a Catalytically Generated Umpolung Reagent through the Use of Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral Vicinal Aminoalcohol Synthons.”
Gargaro, S. L.; Klake, R. K.; Burns, K. L.; Elele, S. O.; Gentry, S. L.; Sieber, J. D. Org. Lett. 2019, 21, 9753 – 9758.
32. “Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents.”
Klake, R. K.; Gargaro, S. L.; Gentry, S. L.; Elele, S. O.; Sieber, J. D. Org. Lett. 2019, 21, 7992 – 7998.
31. “Addition of Non-Stabilized Carbon-Based Nucleophilic Reagents to Chiral N-Sulfinyl Imines.”
Herbage, M. A.; Savoie, J.; Sieber, J. D.; Desrosiers, J. -N.; Zhang, Y.; Marsini, M. A.; Fandrick, K. R.; Rivalti, D.; Senanayake, C. H. Organic Reactions 2019, 1 – 422.
30. ” Application of a Preformed Pd-BIDIME Precatalyst to Suzuki-Miyaura Cross-Coupling Reactions in Flow.”
Sieber, J. D.; Buono, F.; Brusoe, A.; Desrosiers, J. –N.; Haddad, N.; Lorenz, J. C.; Xu, Y.; Wu, H.; Zhang, L.; Han, Z. S.; Roschangar, F.; Song, J. J.; Yee, N. K.; Senanayake, C. H. J. Org. Chem. 2019, 84, 4926 – 4931.
29. “Computationally Assisted Mechanistic Investigation and Development of Pd-Catalyzed Asymmetric Suzuki–Miyaura and Negishi Cross-Coupling Reactions for Tetra-ortho-Substituted Biaryl Synthesis.”
Patel, N. D.; Sieber, J. D.; Tcyrulnikov, S.; Simmons, B. J.; Rivalti, D.; Duvvuri, K.; Zhang, Y.; Gao, D. A.; Fandrick, K. R.; Haddad, N.; Lao, K. S.; Mangunuru, H. P. R.; Biswas, S.; Qu, B.; Grinberg, N.; Pennino, S.; Lee, H.; Song, J. J.; Gupton, B. F.; Garg, N. K.; Kozlowski, M. C.; Senanayake, C. H. ACS Catalysis 2018, 8, 10190 – 10209.
28. “Development of a Scalable, Chromatography-Free Synthesis of t-Bu-SMS-Phos and Application to the Synthesis of an Important Chiral CF3-Alcohol Derivative in High Enantioselectivity Using Rh-Catalyzed Asymmetric Hydrogenation.”
Sieber, J. D.; Rodriguez, S.; Frutos, R.; Buono, F.; Zhang, Y.; Li, N.; Qu, B.; Premasiri, A.; Li, Z.; Han, Z. H.; Xu, Y.; Byrne, D.; Haddad, N.; Lorenz, J.; Grinberg, N.; Kurouski, D.; Lee, H.; Narayanan, B.; Nummy, L.; Mulder, J.; Brown, J. D.; Granger, A.; Gao, J.; Krawiec, M.; Williams, Z.; Pennino, S.; Song, J. J.; Hossain, A.; Yee, N. K.; Busacca, C.; Roschangar, F.; Xin, Y.; Mao, Z.; Zhang, X.; Hong, Y.; Senanayake, C. H. J. Org. Chem. 2018, 83, 1448 – 1461.
27. “Enantioselective Synthesis of a-(Hetero)aryl Piperidines throught Asymmetric Hydrogenation of Pyridinium Salts and Its Mechansistic Insights”
Qu, B.; Mangunuru, H. P. R.; Tcyrulnikov, S.; Rivalti, D.; Zatolochnaya, O. V.; Kurouski, D.; Radomkit, S.; Biswas, S.; Karyakarte, S.; Fandrick, D. R.; Sieber, J. D.; Rodriguez, S.; Desrosiers, J. –N.; Haddad, N.; McKellop, K.; Pennino, S.; Lee, H.; Yee, N. K.; Song, J. J.; Kozlowski, M. C.; Senanayake, C. H. Org. Lett. 2018, 20, 1333 – 1337.
26. “BABIPhos Family of Biaryl Dihydrobenzooxaphosphole Ligands for Asymmetric Hydrogenation.”
Li, G.; Zatolochnaya, V.; Wang, X. –J.; Rodriguez, S.; Qu, B.; Desrosiers, J. –N.; Mangunuru, G. P. R.; Biswas, S.; Rivalti, D.; Karyakarte, S. D.; Sieber, J. D.; Grinberg, N.; Wu, L.; Lee, H.; Haddad, N.; Fandrick, D. R.; Yee, N. K.; Song, J. J.; Senanayake, C. H. Org. Lett. 2018, 20, 1725 – 1729.
25. “Copper-Catalyzed Asymmetric Hydrogenation of 2-Substituted Ketones via Dynamic Kinetic Resolution.”
Zatolochnaya, O. V.; Rodriguez, S.; Zhang, Y.; Lao, K. S.; Tcyrulnikov, S; Si, G.; Wang, X. –J.; Qu, B.; Biswas, S.; Mangunuru, H. P. R.; Rivalti, D. R.; Sieber, J. D.; Desrosiers, J. –N.; Leung, J. C.; Grinberg, N.; Lee, H.; Haddad, N.; Yee, N. K.; Song, J. J.; Kozlowski, M. C.; Senanayake, C. H. Chem. Sci 2018, 9, 4505 – 4510.
24. “Modular Dihydrobenzoazaphosphole Ligands for Suzuki-Miyaura Cross-Coupling.”
Zhang, Y.; Lao, K. S.; Sieber, J. D.; Xu, Y.; Wu, L.; Wang, X. –J.; Desrosiers, J. –N.; Lee, H.; Haddad, N.; Han, Z. S.; Yee, N. K.; Song, J. J.; Howell, A. R.; Senanayake, C. H. Synthesis 2018, 50, 4429 – 4434.
Special issue in honor of Prof. Scott Denmark’s 65th birthday
23. “Effective BI-DIME Ligand for Suzuki-Miyaura Cross-Coupling Reactions in Water with 500 ppm Palladium Loading and Triton X.”
Patel, N. D.; Rivalti, D.; Buono, F. G.; Chatterjee, A.; Qu, B.; Braith, S.; Desrosiers, J. –N.; Rodriguez, S.; Sieber, J. D.; Haddad, N.; Fandrick, K. R.; Lee, H.; Yee, N. K.; Busacca, C. A.; Senanayake, C. H. Asian J. Org. Chem. 2017, 6, 1285 – 1291.
22. “Ligand Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds.”
Zhu, R. –Y.; Saint-Denis, Y. G.; Shao, Y.; He, J.; Sieber, J. D.; Senanayake, C. H.; Yu, J. –Q. J. Am. Chem. Soc. 2017, 139, 5724 – 5727.
21. “Rhodium-Catalyzed Asymmetric Allenylation of Sulfonylimines and Application to the Stereospecific Allylic Allenylation”
Sieber, J. D.; Angeles-Dunham, V. V.; Chennamadhavuni, D.; Fandrick, D. R.; Haddad, N.; Grinberg, N.; Kurouski, D.; Lee, H.; Song, J. J.; Yee, N. K.; Mattson, A. E.; Senanayake, C. H. Adv. Synth. & Catal. 2016, 358, 3062 – 3068.
20. “Rh-Catalysed Asymmetric Conjugate Addition of Boronic Acids to Nitroalkenes Employing a P-Chiral P,π–Hybrid Ligand.”
Sieber, J. D.; Rivalti, D.; Herbage, M. A.; Masters, J. T.; Fandrick, D. R.; Fandrick, D. R.; Haddad, N.; Lee, H.; Yee, N. K.; Gupton, B. F.; Senanayake, C. H. Org. Chem. Front. 2016, 3, 1149 – 1153.
Special issue in honor of Prof. Barry Trost’s 75th birthday
19. “Synthesis of P-Chiral Dihydrobenzooxaphospholes Through Negishi Cross-Coupling.”
Sieber, J. D.; Qu, B.; Rodriguez, S.; Haddad, N.; Grinberg, N.; Lee, H.; Song, J. J.; Yee, N. K.; Senanayake, C. H. J. Org. Chem. 2016, 81, 729 – 736.
18. “Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives Through Asymmetric Reduction of Pyridinium Salts.”
Qu, B.; Mangunuru, H. P. R.; Wei, X.; Fandrick, K. R.; Desrosiers, J. –N.; Sieber, J. D.; Kurouski, D.; Haddad, N.; Samankumara, L. P.; Lee, H.; Savoie, J.; Ma, S.; Grinberg, N.; Sarvestani, M.; Yee, N. K.; Song, J. J.; Senanayake, C. H. Org. Lett. 2016, 18, 4920 – 4923.
17. “Ligand-Accelerated Stereoretentive Suzuki-Miyaura Coupling of Unprotected 3,3’-Dibromo-BINOL.”
Qu, B.; Haddad, N.; Rodriguez, S.; Sieber, J. D.; Desrosiers, J. –N.; Patel, N. D.; Zhang, Y.; Grinberg, N.; Lee, H.; Ma, S.; Ries, U. J.; Yee, N. K.; Senanayake, C. H. J. Org. Chem. 2016, 81, 745 – 750.
16. “Reengineered BI-DIME Ligand Core Based on Computer Modeling to Increase Selectivity in Asymmetric Suzuki-Miyaura Coupling for the Challenging Axially Chiral HIV Integrase Inhibitor.”
Haddad, N.; Mangunuru, H. P. R.; Fandrick, K. R.; Qu, B.; Sieber, J. D.; Rodriguez, S.; Desrosiers, J. –N.; Patel, N. D.; Lee, H.; Kurouski, D.; Grinberg, N.; Yee, N. K.; Song, J. J.; Senanayake, C. H. Adv. Synth. & Catal. 2016, 358, 3522 – 3527.
15. “Rh-Catalyzed Reagent-Free Ring Expansion of Cycobutenones and Benzocyclobutenones.”
Chen, P. -H.; Sieber, J. D.; Senanayake, C. H.; Dong, G. Chem. Sci. 2015, 6, 5440 – 5445.
14. “Efficient Asymmetric Synthesis of Structurally Diverse P-Stereogenic Phosphinamides for Catalyst Design.”
Han, Z. S.; Zhang, L.; Xu, Y.; Sieber, J. D.; Marsini, M. A.; Li, Z.; Reeves, J. T. ; Fandrick, K. R. ; Patel, N. D. ; Desrosiers, J. –N. ; Qu, B. ; Chen, A. ; Rudzinski, D. M. ; Samankumara, L. P. ; Ma, S. ; Grinberg, N. ; Roschangar, F. ; Yee, N. K. ; Wang, G. ; Song, J. J. ; Senanayake, C. H. Angew. Chem. Int. Ed. 2015, 54, 5474 – 5477.
13. “Development of a Practical Sequence for Difluoromethylation of 2-Bromopyridines via Copper-Mediated Reductive Coupling and Decarboxylation.”
Zeng, X.; Wei, X.; Song, J. J.; Sarvestani, M.; Fandrick, D. R.; Qu, B.; Rodriguez, S.; Sieber, J. D.; Desrosiers, J. –N.; Yee, N. K.; Roschangar, F.; Senanayake, C. H. Asian J. Org. Chem. 2015, 4, 1262 – 1264.
12.“Copper-Catalyzed Electrophilic Amination of Heteroaromatic and Aromatic C-H Bonds via TMPZnCl-LiCl Mediated Metalation.”
McDonald, S. L.; Hendrick, C. E.; Bitting, K. J.; Wang, Q.; Sieber, J. D.; Senanayake, C. H. Org. Synth. 2015, 92, 356 – 372.
11. “Development of New P-Chiral P,π-Dihydrobenzooxaphosphole Hybrid Ligands for Asymmetric Catalysis.”
Sieber, J. D.; Chennamadhavuni, D.; Fandrick, K. R.; Qu, B.; Han, Z. S.; Savoie, J.; Ma, S.; Samankumara, L. P.; Grinberg, N.; Lee, H.; Song, J. J.; Senanayake, C. H. Org. Lett. 2014, 16, 5494 – 5497.
10. “Design and Synthesis of Chiral Oxathiazinone Scaffolds: Efficient Synthesis of Hindered Enantiopure Sulfinamides and Sulfinyl Ketimines.”
Han, Z. S.; Herbage, M. A.; Manganuru, H. P. R.; Xu, Y.; Zhang, L.; Reeves, J. T.; Sieber, J. D.; Li, Z.; Decroos, P.; Zhang, Y.; Li, G.; Li, N.; Ma, S.; Grinberg, N.; Wang, X.; Goyal, N.; Krishnamurthy, D.; Lu, B.; Song, J. J.; Wang, G.; Senanayake, C. H. Angew. Chem. Int. Ed. 2013, 52, 6713 – 6717.
9. “Efficient Asymmetric Synthesis of P-Chiral Phosphine Oxides via Properly Designed and Activated Benzoxazaphosphinine-2-oxide Agents.”
Han, Z. S.; Goyal, N.; Herbage, M. A.; Sieber, J. D.; Qu, B.; Xu, Y.; Li, Z.; Reeves, J. T.; Desrosiers, N. –D.; Ma, S.; Grinberg, N.; Lee, H.; Mangunuru, G. P. R.; Zhang, Y.; Krishnamurthy, D.; Lu, B. Z.; Song, J. J.; Wang, G.; Senanayake, C. H. J. Am. Chem. Soc. 2013, 135, 2474 – 2477.
Graduate and Postdoctoral:
8. “The Palladium Catalyzed Asymmetric Addition of Oxindoles and Allenes: an Atom-Economical Versatile Method for the Construction of Chiral Indole Alkaloids.”
Trost, B. M.; Xie, J.; Sieber, J. D. J. Am. Chem. Soc. 2011, 133, 20611 – 20622.
7. “Catalytic Enantioselective Conjugate Allylation of Unsaturated Methylidene Ketones.”
Brozek, L. A.; Sieber, J. D.; Morken, J. P. Org. Lett. 2011, 13, 995 – 997.
6. “Catalytic Asymmetric Allylic Alkylation Employing Heteroatom Nucleophiles: A Powerful Method for C-X Bond Formation.”
Trost, B. M.; Zhang, T.; Sieber, J. D. Chem. Sci. 2010, 1, 427 – 440.
5. “Asymmetric Total Synthesis of Soraphen A: A Flexible Alkyne Strategy.”
Trost, B. M.; Sieber, J. D.; Qian, W.; Dhawan, R.; Ball, Z. T. Angew. Chem. Int. Ed. 2009, 48, 5478 – 5481; Angew. Chem. 2009, 121, 5586 – 5589.
4. “Ni-Catalyzed Asymmetric Conjugate Allylation of Activated Enones.”
Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2008, 130, 4978 – 4983.
3. “Catalytic Conjugate Addition of Allyl Groups to Styryl-Activated Enones.”
Sieber, J. D.; Liu, S.; Morken, J. P. J. Am. Chem. Soc. 2007, 129, 2214 – 2213.
2. “Sequential Pd-Catalyzed Asymmetric Allene Dibroation/α-Aminoallylation.”
Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2006, 128, 74 – 75.
1. “Palladium-Catalyzed Enantioselective Dibroation of Prochiral Allenes”Pelz, N. F.; Woodward, A. R.; Burks, H. E.; Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 16328 – 16329.
Patents:
3. “Preparation of spiro(cyclobutanol-pyrrolidinyl) diacylhydrazines as drug intermediates.” Beyer, P.; Brazzillo, J. A.; Eriksson, M.; Lorenz, J. C.; Nummy, L. J.; Rodriguez, S.; Savoie, J.; Sidhu, K. P. S.; Sieber, J. D.; Tampone, T. G.; Tan, Z.; Wang, J.; Zhang, L. WO 2019027860 A1 issued Feb. 07, 2019.
2. “Novel Chiral Dihydrobenzooxaphosphole Ligands and Synthesis Thereof.”
Desrosiers, J. –N.; Fandrick, D. R.; Haddad, N.; Li, G.; Patel, N. D.; Qu, B.; Rodriguez, S.; Senanayake, C. H.; Sieber, J. D.; Tan, Z.; Wang, X. –J.; Yee, N. K.; Li, Z.; Zhang, Y. U.S. Patent # 20180155375 A1 issued June 07, 2018.
1. “Novel Chiral Dihydrobenzoazaphosphole Ligands and Synthesis Thereof.”
Biswas, S.; Desrosiers, J. –N.; Lao, K.; Mangunuru, H. P. R.; Qu, B.; Rodriguez, S.; Senanayake, C. H.; Sieber, J. D.; Wang, X. –J.; Yee, N. K.; Zhang, Y. U.S. Patent # 20180155377 A1 issued June 07, 2018.
Sieber Research Group 