Stereospecific ring expansion from orthocyclophanes with central chirality to metacyclophanes with planar chirality

Nature Communications

Volumn 5, Issue , 2014, Pages

  Ishida, Naoki ^a   Sawano, Shota ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CYCLOPHANE DERIVATIVE; HAEMOPHILUS INFLUENZAE TYPE B VACCINE; HYDROGEN; HYDROXYL GROUP; RHODIUM;

CARBON; CATALYST; CHEMICAL BONDING; CRYSTALLIZATION; THERMODYNAMICS;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHIRALITY; COVALENT BOND; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; LIGHT; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; RING OPENING; STEREOISOMERISM; STEREOSPECIFICITY; SYNTHESIS; THERMODYNAMICS;

EID: 84896787034     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms4111     Document Type: Article

References (50)

1. Rybtchinski, B. & Milstein, D. Metal insertion into C-C bonds in solution. Angew. Chem. Int. Ed. 38, 870-883 (1999).
2. Murakami, M. & Ito, Y. in Activation of Unreactive Bonds and Organic Synthesis. (ed Murai, S.) 97-129 (Springer, 1999).
3. Takahashi, T., Kotora, M., Hara, R. & Xi, Z. Carbon-carbon bond cleavage and selective transformation of zirconacycles. Bull. Chem. Soc. Jpn 72, 2591-2602 (1999).
4. Perthuisot, C. et al. Cleavage of the carbon-carbon bond in biphenylene using transition metals. J. Mol. Cat. A 189, 157-168 (2002).
5. Jun, C.-H. Transition metal-catalyzed carbon-carbon bond activation. Chem. Soc. Rev. 33, 610-618 (2004).
6. Satoh, T. & Miura, M. in Palladium in Organic Synthesis. (ed Tsuji, J.) 1-20 (Springer, 2005).
7. Kondo, T. & Mitsudo, T. Ruthenium-catalyzed reconstructive synthesis of functional organic molecules via cleavage of carbon-carbon bonds. Chem. Lett 34, 1462-1467 (2005).
8. Nečas, D. & Kotora, M. Rhodium-catalyzed C-C bond cleavage reactions. Curr. Org. Chem. 11, 1566-1591 (2007).
9. Tobisu, M. & Chatani, N. Catalytic reactions involving the cleavage of carbon-cyano and carbon-carbon triple bonds. Chem. Soc. Rev. 37, 300-307 (2008).
10. Nakao, Y. & Hiyama, T. Nickel-catalyzed carbocyanation of alkynes. Pure Appl. Chem. 80, 1097-1107 (2008).
11. Yorimitsu, H. & Oshima, K. Metal-mediated retro-allylation of homoallyl alcohols for highly selective organic synthesis. Bull. Chem. Soc. Jpn 82, 778-792 (2009).
12. Seiser, T. & Cramer, N. Enantioselective metal-catalyzed activation of strained rings. Org. Biomol. Chem. 7, 2835-2840 (2009).
13. Aïssa, C. Transition-metal-catalyzed rearrangements of small cycloalkanes: Regioselectivity trends in b-carbon elimination reactions. Synthesis (Mass) 3389-3407 (2011).
14. Ruhland, K. Transition-metal-mediated cleavage and activation of C-C Single bonds. Eur. J. Org. Chem. 2012, 2683-2706 (2012).
15. Dong, G. Ketone-based transition-metal-catalyzed carbon-carbon and carbon-hydrogen bond activation: exploratory studies. Synlett 24, 1-5 (2013).
16. Kakiuchi, F. & Murai, S. in Activation of Unreactive Bonds and Organic Synthesis. (ed Murai, S.) 45-79 (Springer, 1999).
17. Colby, D. A., Bergman, R. G. & Ellman, J. A. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation. Chem. Rev. 110, 624-655 (2010).
18. Mkhalid, I. A. I., Barnard, J. H., Marder, T. B., Murphy, J. M. & Hartwig, J. F. CH activation for the construction of C-B bonds. Chem. Rev. 110, 890-931 (2010).
19. Lyons, T. W. & Sanford, M. S. Palladium-catalyzed ligand-directed C-H functionalization reactions. Chem. Rev. 110, 1147-1169 (2010).
20. Newhouse, T. & Baran, P. S. If C-H bonds could talk: selective C-H bond oxidation. Angew. Chem. Int. Ed. 50, 3362-3374 (2011).
21. Ackermann, L. Carboxylate-assisted transition-metal-catalyzed C-H bond functionalizations: mechanism and scope. Chem. Rev. 111, 1315-1345 (2011).
22. Engle, K. M., Mei, T., Wasa, M. & Yu, J. Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions. ACC Chem. Res. 45, 788-802 (2012).
23. Yamaguchi, J., Yamaguchi, A. D. & Itami, K. C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals. Angew. Chem. Int. Ed. 51, 8960-9009 (2012).
24. Arockiam, P. B., Bruneau, C. & Dixneuf, P. H. Ruthenium(II)-catalyzed C-H bond activation and functionalization. Chem. Rev. 112, 5879-5918 (2012).
25. Wencel-Delord, J. & Glorius, F. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules. Nat. Chem. 5, 369-375 (2013).
26. Gleiter, R. & Hopf, H ed. Modern Cyclophane Chemistry (Wiley-VCH, 2004).
27. Gulder, T. & Baran, P. S. Strained cyclophane natural products: macrocyclization at its limits. Nat. Prod. Rep. 29, 899-934 (2012).
28. Driggers, E. M., Hale, S. P., Lee, J. & Terrett, N. K. The exploration of macrocycles for drug discovery-an underexploited structural class. Nat. Rev. Drug Discov. 7, 608-624 (2008).
29. Marsault, E. & Peterson, M. Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery. J. Med. Chem. 54, 1961-2004 (2011).
30. Droz, A. S., Neidlein, U., Anderson, S., Seiler, P. & Diederich, F. Optically active cyclophane receptors for mono- and disaccharides: the role of bidentate ionic hydrogen bonding in carbohydrate recognition. Helv. Chim. Acta 84, 2243-2289 (2001).
31. Ramaiah, D., Neelakandan, P. P., Nair, A. K. & Avirah, R. R. Functional cyclophanes: promising hosts for optical biomolecular recognition. Chem. Soc. Rev. 39, 4158-4168 (2010).
32. Lindoy, L. F., Park, K.-M. & Lee, S. S. Metals, macrocycles and molecular assemblies - macrocyclic complexes in metallo-supramolecular chemistry. Chem. Soc. Rev. 42, 1713-1727 (2013).
33. Kane, V. V., Wolf, W. H. & De & Bickelhaupt, F. Synthesis of small cyclophanes. Tetrahedron 50, 4575-4622 (1994).
34. Mori, K., Ohmori, K. & Suzuki, K. Hydrogen-bond control in axially chiral styrenes: selective synthesis of enantiomerically pure C2-symmetric paracyclophanes. Angew. Chem., Int. Ed. 48, 5638-5641 (2009).
35. Kanomata, N., Mishima, G. & Onozato, J. Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation. Tetrahedron Lett. 50, 409-412 (2009).
36. Kanda, K., Hamanaka, R., Endo, K. & Shibata, T. Asymmetric ortho-lithiation of 1, n-dioxa[n]paracyclophane derivatives for the generation of planar chirality. Tetrahedron 68, 1407-1416 (2012).
37. Shibata, T. et al. Enantioselective synthesis of tripodal cyclophanes and pyridinophanes by intramolecular [2+2+2] cycloaddition. Tetrahedron 68, 2679-2686 (2012).
38. Araki, T., Noguchi, K. & Tanaka, K. Enantioselective synthesis of planar-chiral carba-paracyclophanes: rhodium-catalyzed [2+2+2] cycloaddition of cyclic diynes with terminal monoynes. Angew. Chem., Int. Ed. 52, 5617-5621 (2013).
39. Matsuura, T. & Kitaura, Y. Photochemical reaction of hindered aromatic ketones. Tetrahedron Lett. 8, 3309-3310 (1967).
40. Carré, M.-C., Viriot-Villaume, M.-L. & Caubére, P. Synthetic photochemistry. Part 2. Generation of benzocyclobutenols by photocyclisation of benzocycloalkenones. J. Chem. Soc. Perkin 1, 2542-2549 (1979).
41. Wagner, P. J., Subrahmanyam, D. & Park, B.-S. The mechanism for the photocyclization of o-alkyl ketones to cyclobutenols. J. Am. Chem. Soc. 113, 709-710 (1991).
42. Chtchemelinine, A., Rosa, D. & Orellana, A. Palladium-catalyzed selective carboelimination and cross-coupling reactions of benzocyclobutenols with aryl bromides. J. Org. Chem. 76, 9157-9162 (2011).
43. Rosa, D., Chtchemelinine, A. & Orellana, A. Tandem decarboxylative allylation and fragmentation of allyl benzocyclobutenyl carbonates: Access to orthofunctionalized aryls from aryl Bromides. Synthesis (Mass) 44, 1885-1891 (2012).
44. Ishida, N., Sawano, S., Masuda, Y. & Murakami, M. Rhodium-catalyzed ring opening of benzocyclobutenols with site-selectivity complementary to thermal ring opening. J. Am. Chem. Soc. 134, 17502-17504 (2012).
45. Matsuda, T. & Miura, N. Synthesis of tetrasubstituted benzenes via rhodium(I)- catalysed ring-opening benzannulation of cyclobutenols with alkynes. Org. Biomol. Chem. 11, 3424-3427 (2013).
46. Haag, R., Wirz, J. & Wagner, P. J. The photoenolization of 2-methylacetophenone and related compounds. Helv. Chim. Acta 60, 2595-2607 (1977).
47. Das, P. K., Encinas, M. V., Small, Jr R. D. & Scaiano, J. C. Photoenolization of o-alkyl-substituted carbonyl compounds. Use of electron transfer processes to characterize transient intermediates. J. Am. Chem. Soc. 101, 6965-6970 (1979).
48. Yang, N. C. & Rivas, C. A new photochemical primary process, the photochemical enolization of o-substituted benzophenones. J. Am. Chem. Soc. 83, 2213 (1961).
49. Zhao, P., Incarvito, C. D. & Hartwig, J. F. Direct observation of b-aryl eliminations from Rh(I) alkoxides. J. Am. Chem. Soc. 128, 3124-3125 (2006).
50. Burns, N. Z., Krylova, I. N., Hannoush, R. N. & Baran, P. S. Scalable total synthesis and biological evaluation of haouamine A and its atropisomer. J. Am. Chem. Soc. 131, 9172-9173 (2009).