Air- and moisture-stable amphoteric molecules: Enabling reagents in synthesis

Accounts of Chemical Research

Volumn 47, Issue 4, 2014, Pages 1029-1040

  He, Zhi ^a   Zajdlik, Adam ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; AZIRIDINE; AZIRIDINE DERIVATIVE; BORON DERIVATIVE; CYANIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ETHER DERIVATIVE;

AIR; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AIR; ALCOHOLS; ALDEHYDES; AZIRIDINES; BORON COMPOUNDS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYANIDES; ETHERS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE;

EID: 84898878174     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar400210c     Document Type: Article

References (51)

1. Colange, L. Zell's popular encyclopedia; a universal dictionary of English language, science, literature and art; T. E. Zell: Philadelphia, 1871.
2. Samarakoon, T. B.; Hur, M. Y.; Kurtz, R. D.; Hanson, P. R. A Formal [4 + 4] Complementary Ambiphile Pairing Reaction: A New Cyclization Pathway for ortho-Quinone Methides Org. Lett. 2010, 12, 2182-2185
3. Rolfe, A.; Samarakoon, T. B.; Hanson, P. R. Formal [4 + 3] Epoxide Cascade Reaction via a Complementary Ambiphilic Pairing Strategy Org. Lett. 2010, 12, 1216-1219
4. Multicomponent Reactions; Zhu, J.; Bienaymé, H., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005.
5. Jebrail, M. J.; Ng, A. H. C.; Rai, V.; Hili, R.; Yudin, A. K.; Wheeler, A. R. Synchronized Synthesis of Peptide-Based Macrocycles by Digital Microfluidics Angew. Chem., Int. Ed. 2010, 49, 8625-8629
6. Scully, C. C. G.; Rai, V.; Poda, G.; Zaretsky, S.; Burns, D. C.; Houliston, R. S.; Lou, T.; Yudin, A. K. Bending Rigid Molecular Rods: Formation of Oligoproline Macrocycles Chem.-Eur. J. 2012, 18, 15612-15617
7. Roxin, á.; Chen, J.; Scully, C. C. G.; Rotstein, B. H.; Yudin, A. K.; Zheng, G. Conformational Modulation of in Vitro Activity of Cyclic RGD Peptides via Aziridine Aldehyde-Driven Macrocyclization Chemistry Bioconjugate Chem. 2012, 23, 1387-1395
8. Rotstein, B. H.; Winterheimer, D. J.; Yin, L. M.; Deber, C. M.; Yudin, A. K. Thioester-Isocyanides: Versatile Reagents for the Synthesis of Cycle-Tail Peptides Chem. Commun. 2012, 48, 3775-3777
9. Rotstein, B. H.; Rai, V.; Hili, R.; Yudin, A. K. Synthesis of Peptide Macrocycles Using Unprotected Amino Aldehydes Nat. Protoc. 2010, 5, 1813-1822
10. Layer, R. W. The Chemistry of Imines Chem. Rev. 1963, 63, 489-510
11. Fischer, E.; Leuchs, H. Synthesis of d -Glucosamine Ber. Dtsch. Chem. Ges. 1903, 36, 24-29
12. Myers, A. G.; Kung, D. W.; Zhong, B. Observations Concerning the Existence and Reactivity of Free α-Amino Aldehydes as Chemical Intermediates: Evidence for Epimerization-Free Adduct Formation with Various Nucleophiles J. Am. Chem. Soc. 2000, 122, 3236-3237
13. Ooi, T.; Saito, A.; Maruoka, K. Asymmetric Skeletal Rearrangement of Symmetrically α,α-Disubstituted α-Amino Aldehydes: A New Entry to Optically Active α-Hydroxy Ketones J. Am. Chem. Soc. 2003, 125, 3220-3221
14. Rabourn, W. J.; Howard, W. L. Aminohydrins from Aziridine J. Org. Chem. 1962, 27, 1039-1041
15. Manecke, G.; Heller, H. Über einige neue Ä thyleniminverbindungen Chem. Ber. 1962, 95, 2700-2707
16. Hili, R.; Yudin, A. K. Readily Available Unprotected Amino Aldehydes J. Am. Chem. Soc. 2006, 128, 14772-14773
17. Assem, N.; Hili, R.; He, Z.; Kasahara, T.; Inman, B. L.; Decker, S.; Yudin, A. K. Control of Carbonyl Reactivity Using Reversible Covalent Interactions J. Org. Chem. 2012, 77, 5613-5623
18. Hodgson, D. M.; Humphreys, P. G.; Xu, Z.; Ward, J. G. Lithiation-Induced Migrations from Nitrogen to Carbon in Terminal Aziridines Angew. Chem., Int. Ed. 2007, 46, 2245-2248
19. Li, X.; Yudin, A. K. Epimerization- and Protecting-Group-Free Synthesis of Peptidomimetic Conjugates from Amphoteric Amino Aldehydes J. Am. Chem. Soc. 2007, 129, 14152-14153
20. Liew, S. K.; He, Z.; St. Denis, J. D.; Yudin, A. K. Stereocontrolled Synthesis of 1,2- and 1,3-Diamine Building Blocks from Aziridine Aldehyde Dimers J. Org. Chem. 2013, 78, 11637-11645
21. Hili, R.; Yudin, A. K. Amphoteric Amino Aldehydes Enable Rapid Assembly of Unprotected Amino Alcohols Angew. Chem., Int. Ed. 2008, 47, 4188-4191
22. Baktharaman, S.; Afagh, N.; Vandersteen, A.; Yudin, A. K. Unprotected Vinyl Aziridines: Facile Synthesis and Cascade Transformations Org. Lett. 2010, 12, 240-243
23. He, Z.; Yudin, A. K. A Versatile Synthetic Platform Based on Strained Propargyl Amines Angew. Chem., Int. Ed. 2010, 49, 1607-1610
24. Cox, E. D.; Cook, J. M. The Pictet-Spengler Condensation: A New Direction for an Old Reaction Chem. Rev. 1995, 95, 1797-1842
25. Hili, R.; Rai, V.; Yudin, A. K. Macrocyclization of Linear Peptides Enabled by Amphoteric Molecules J. Am. Chem. Soc. 2010, 132, 2889-2891
26. Failli, A.; Immer, H.; Gotz, M. The Synthesis of Cyclic Peptides by the Four Component Condensation (4 CC) Can. J. Chem. 1979, 57, 3257-3161
27. Cheung, L. L. W.; He, Z.; Decker, S. M.; Yudin, A. K. Skeletal Fusion of Small Heterocycles with Amphoteric Molecules Angew. Chem., Int. Ed. 2011, 47, 11798-11802
28. Hili, R.; Yudin, A. K. Amphoteric Amino Aldehydes Reroute the Aza-Michael Reaction J. Am. Chem. Soc. 2009, 131, 16404-16406
29. Larson, G. L. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 3, p 105.
30. 5BO Potential Energy Surface, the Barrier to 1,3-Shifts in β-Ketoboranes, and the Mechanism of the Carbonylation Reaction of Boranes J. Comput. Chem. 1992, 13, 423-428
31. Sucrow, W.; Zühlke, L.; Slopianka, M.; Pickardt, J. Enehydrazines, 16. Stable Boranes from Enehydrazones Chem. Ber. 1977, 110, 2818-2833
32. Paetzold, P.; Kosma, S. Boration Reactions of Ketene Chem. Ber. 1979, 112, 654-662
33. 2CHC(Me)O J. Organomet. Chem. 1990, 396, 253-267
34. 2 J. Organomet. Chem. 1993, 444, 5-14
35. Denniel, V.; Bauchat, P.; Toupet, L.; Carboni, B.; Danion, D.; Danion-Bougot, R. Hydroboration of Methyl 2-Acetamidoacrylate. Characterisation and Nucleophilic Reactivity of the Resulting Oxytriorganoborate Tetrahedron Lett. 1995, 36, 3507-3510
36. Denniel, V.; Bauchat, P.; Carboni, B.; Danion, D.; Danion-Bougot, R. Hydroboration of Methyl 2-Acetamidoacrylate. II-New Aspects of the Reactivity of the Resulting Oxytriorganoborates Tetrahedron Lett. 1995, 36, 6875-6878
37. He, Z.; Yudin, A. K. Amphoteric α-Boryl Aldehydes J. Am. Chem. Soc. 2011, 133, 13770-13773
38. 3) Boronate Building Blocks J. Am. Chem. Soc. 2011, 133, 13774-13777
39. St. Denis, J. D.; He, Z.; Yudin, A. K. Chemoselective Palladium-Catalyzed α-Allylation of α-Boryl Aldehydes Org. Biomol. Chem. 2012, 10, 7900-7902
40. He, Z.; Zajdlik, A.; St. Denis, J. D.; Assem, N.; Yudin, A. K. Boroalkyl Group Migration Provides a Versatile Entry into α-Aminoboronic Acid Derivatives J. Am. Chem. Soc. 2012, 134, 9926-9929
41. Zajdlik, A.; Wang, Z.; Hickey, J. L.; Aman, A.; Schimmer, A. D.; Yudin, A. K. α-Boryl Isocyanides Enable Facile Preparation of Bioactive Boropeptides Angew. Chem., Int. Ed. 2013, 52, 8411-8415
42. Greener, B.; Millan, D. S. In Modern Drug Synthesis; Li, J. J.; Johnson, D. S., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, 2010; Chapter 8, pp 99-110.
43. Dumas, A. M.; Molander, G. A.; Bode, J. W. Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water Angew. Chem., Int. Ed. 2012, 51, 5683-5686
44. Dumas, A. M.; Bode, J. W. Synthesis of Acyltrifluoroborates Org. Lett. 2012, 14, 2138-2141
45. Molander, G. A.; Raushel, J.; Ellis, N. M. Synthesis of an Acyltrifluoroborate and its Fusion with Azides to Form Amides J. Org. Chem. 2010, 75, 4304-4306
46. Monot, J.; Solovyev, A.; Bonin-Dubarle, H.; Derat, é.; Curran, D. P.; Robert, M.; Fensterbank, L.; Malacria, M.; Lacôte, E. Generation and Reactions of an Unsubstituted N -Heterocyclic Carbene Boryl Anion Angew. Chem., Int. Ed. 2010, 49, 9166-9169
47. Segawa, Y.; Suzuki, Y.; Yamashita, M.; Nozaki, K. Chemistry of Boryllithium: Synthesis, Structure, and Reactivity J. Am. Chem. Soc. 2008, 130, 16069-16079
48. Yamashita, M.; Suzuki, Y.; Segawa, Y.; Nozaki, K. Synthesis, Structure of Borylmagnesium, and Its Reaction with Benzaldehyde to Form Benzoylborane J. Am. Chem. Soc. 2007, 129, 9570-9571
49. Hair, G. S.; Jones, R. A.; Cowley, A. H.; Lynch, V. Insertion and Coordination Reactions of Titanium(IV) Metallocene Zwitterions Organometallics 2001, 20, 177-181
50. Imamoto, T.; Hikosaka, T. Reactions of Phosphine-Monoiodoboranes with 4,4′-Di-tert-butylbiphenylide and Electrophiles. Trial of Generation of Tricoordinate Boron Anions and Synthesis of B-Functionalized Phosphine-Boranes J. Org. Chem. 1994, 59, 6753-6759
51. He, Z.; Trinchera, P.; Adachi, S.; St. Denis, J. D.; Yudin, A. K. Oxidative Geminal Functionalization of Organoboron Compounds Angew. Chem., Int. Ed. 2012, 51, 11092-11096