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Cite the Following Article
Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines
Jian-bo Xie, Jian Luo, Timothy R. Winn, David B. Cordes and Guigen Li
Beilstein J. Org. Chem. 2014, 10, 746–751.
https://doi.org/10.3762/bjoc.10.69
How to Cite
Xie, J.-b.; Luo, J.; Winn, T. R.; Cordes, D. B.; Li, G. Beilstein J. Org. Chem. 2014, 10, 746–751. doi:10.3762/bjoc.10.69
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- Październiok‐Holewa, A.; Stecko, S. doi:10.1002/9783527834204.ch3
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- Wu, G.; Liu, Y.; Rouh, H.; Ma, L.; Tang, Y.; Zhang, S.; Zhou, P.; Wang, J. Y.; Jin, S.; Unruh, D. K.; Surowiec, K.; Ma, Y.; Li, G. Asymmetric Catalytic Approach to Multilayer 3D Chirality. Chemistry – A European Journal 2021, 27, 8013–8020. doi:10.1002/chem.202100700
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- Fan, D.; Zhang, J.; Hu, Y.; Zhang, Z.; Gridnev, I. D.; Zhang, W. Asymmetric Hydrogenation of α-Boryl Enamides Enabled by Nonbonding Interactions. ACS Catalysis 2020, 10, 3232–3240. doi:10.1021/acscatal.9b04543
- Parra, A.; Trulli, L.; Tortosa, M. PATAI'S Chemistry of Functional Groups - Copper‐Catalyzed Addition of Diboron Species. Patai's Chemistry of Functional Groups 2020, 1–82. doi:10.1002/9780470682531.pat0976
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- Bo, L.; Jinqiang, K.; Chen, J.; Zhenguo, H.; Khakyzadeh, V.; Xia, Y. A one-pot protocol for the synthesis of β-ketosulfones from α,α-dibromoketones. Organic Chemistry Frontiers 2019, 6, 2647–2653. doi:10.1039/c9qo00440h
- Wu, G.; Liu, Y.; Yang, Z.; Katakam, N.; Rouh, H.; Ahmed; Unruh, D. K.; Surowiec, K.; Li, G. Multilayer 3D Chirality and Its Synthetic Assembly. Research (Washington, D.C.) 2019, 2019, 6717104. doi:10.34133/2019/6717104
- Hyland, S. N.; Meck, E. A.; Tortosa, M.; Clark, T. α-Amidoboronate esters by amide-directed alkane CH borylation. Tetrahedron Letters 2019, 60, 1096–1098. doi:10.1016/j.tetlet.2019.03.020
- Patel, D. M.; Vala, R. M.; Sharma, M.; Rajani, D. P.; Patel, H. M. A Practical Green Visit to the Functionalized [1,2,4]Triazolo[5,1‐b]quinazolin‐8(4H)one Scaffolds Using the Group‐Assisted Purification (GAP) Chemistry and Their Pharmacological Testing. ChemistrySelect 2019, 4, 1031–1041. doi:10.1002/slct.201803605
- Chen, L.; Shen, J.-J.; Gao, Q.; Xu, S. Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles. Chemical science 2018, 9, 5855–5859. doi:10.1039/c8sc01815d
- Zhang, H.; Yang, Z.; Zhao, B. N.; Li, G. Group-Assisted Purification Chemistry for Asymmetric Mannich-type Reaction of Chiral N-Phosphonyl Imines with Azlactones Leading to Syntheses of α-Quaternary α,β-Diamino Acid Derivatives †. The Journal of organic chemistry 2017, 83, 644–655. doi:10.1021/acs.joc.7b02556
- López, A.; Clark, T.; Parra, A.; Tortosa, M. Copper-Catalyzed Enantioselective Synthesis of β-Boron β-Amino Esters. Organic letters 2017, 19, 6272–6275. doi:10.1021/acs.orglett.7b02784
- Geier, S. J.; LaFortune, J. H. W.; Zhu, D.; Kosnik, S. C.; Macdonald, C. L. B.; Stephan, D. W.; Westcott, S. A. The phosphinoboration of carbodiimides, isocyanates, isothiocyanates and CO2. Dalton transactions (Cambridge, England : 2003) 2017, 46, 10876–10885. doi:10.1039/c7dt02305g
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- SEIFERT COLE. Compositions and methods for chemical synthesis. US 12024537 B2, July 2, 2024.
- REDDY RAJA K; HECKER SCOTT J. Boronic acid derivatives and therapeutic uses thereof. US 12016868 B2, June 25, 2024.
- HECKER SCOTT J; REDDY RAJA K; GLINKA TOMASZ; RODNY OLGA. Boronic acid derivatives and therapeutic uses thereof. US 11999759 B2, June 4, 2024.
- SEIFERT COLE. Synthesis strategy for gap protecting group. US 11827660 B2, Nov 28, 2023.
- HIRST GAVIN; REDDY RAJA; HECKER SCOTT J; TOTROV MAXIM; GRIFFITH DAVID C; LOMOVSKAYA OLGA; DUDLEY MICHAEL N; BOYER SERGE HENRI. Therapeutic uses of pharmaceutical compositions comprising cyclic boronic acid ester derivatives. US 11684629 B2, June 27, 2023.
- LI GUIGEN; SEIFERT COLE. SYSTEM AND METHOD FOR SOLUTION PHASE GAP PEPTIDE SYNTHESIS. EP 4079737 A1, Oct 26, 2022.
- HECKER SCOTT J; BOYER SERGE HENRI; DIELEMANS HUBERTUS J A; GONZALEZ DE CASTRO ANGELA; DE VRIES ANDREAS H M; LEFORT LAURENT. Boronic acid derivatives and synthesis thereof. US 11286270 B2, March 29, 2022.
- HECKER SCOTT J; REDDY RAJA K; GLINKA TOMASZ; RODNY OLGA. Boronic acid derivatives and therapeutic uses thereof. US 11180512 B2, Nov 23, 2021.
- HIRST GAVIN; REDDY RAJA; HECKER SCOTT J; TOTROV MAXIM; GRIFFITH DAVID C; LOMOVSKAYA OLGA; DUDLEY MICHAEL N; BOYER SERGE HENRI. Therapeutic uses of pharmaceutical compositions comprising cyclic boronic acid ester derivatives. US 11090319 B2, Aug 17, 2021.
- LI GUIGEN; SEIFERT COLE. System and method for solution phase gap peptide synthesis. US 10947267 B2, March 16, 2021.
- HECKER SCOTT; BOYER SERGE. Synthesis of boronate salts and uses thereof. US 10669292 B2, June 2, 2020.
- HECKER SCOTT; REDDY RAJA K; GLINKA TOMASZ. Cyclic boronic acid ester derivatives and therapeutic uses thereof. US 10662205 B2, May 26, 2020.
- HIRST GAVIN; REDDY RAJA; HECKER SCOTT; TOTROV MAXIM; GRIFFITH DAVID C; RODNY OLGA; DUDLEY MICHAEL N; BOYER SERGE. Therapeutic uses of pharmaceutical compositions comprising cyclic boronic acid ester derivatives. US 10639318 B2, May 5, 2020.
- HECKER SCOTT; REDDY RAJA K. Substituted boronic acids as antimicrobials. US 10618918 B2, April 14, 2020.
- HECKER SCOTT J; REDDY RAJA K; GLINKA TOMASZ; RODNY OLGA. Boronic acid derivatives and therapeutic uses thereof. US 10570159 B2, Feb 25, 2020.
- SEIFERT COLE. METHOD FOR SOLUTION-PHASE PEPTIDE SYNTHESIS AND PROTECTING STRATEGIES THEREFORE. WO 2019231760 A1, Dec 5, 2019.
- HECKER SCOTT; BOYER SERGE. Synthesis of boronate salts and uses thereof. US 10385074 B2, Aug 20, 2019.
- HECKER SCOTT J; REDDY RAJA K; GLINKA TOMASZ; RODNY OLGA. Boronic acid derivatives and therapeutic uses thereof. US 10294249 B2, May 21, 2019.
- REDDY RAJA K; GLINKA TOMASZ; TOTROV MAXIM; HECKER SCOTT; RODNY OLGA. Boronic acid derivatives and therapeutic uses thereof. US 10206937 B2, Feb 19, 2019.
- HIRST GAVIN; REDDY RAJA; HECKER SCOTT; TOTROV MAXIM; GRIFFITH DAVID C; RODNY OLGA; DUDLEY MICHAEL N; BOYER SERGE. Therapeutic uses of pharmaceutical compositions comprising cyclic boronic acid ester derivatives. US 10183034 B2, Jan 22, 2019.