Organocatalytic stereoselective [8+2] and [6+4] cycloadditions

Nature Chemistry

Volumn 9, Issue 5, 2017, Pages 487-492

  Mose, Rasmus ^a   Preegel, Gert ^a   Larsen, Jesper ^a   Jakobsen, Sofie ^a   Iversen, Eva Høgh ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85018457922     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2682     Document Type: Article

References (42)

1. Woodward, R. B. & Hoffmann, R. Stereochemistry of electrocyclic reactions. J. Am. Chem. Soc. 87, 395-397 (1965).
2. Doering, W., von, E. &Wiley, D.W. Heptafulvene (methylenecycloheptatriene). Tetrahedron 11, 183-198 (1960).
3. Hoffmann, R. & Woodward, R. B. Selection rules for concerted cycloaddition reactions. J. Am. Chem. Soc. 87, 2046-2048 (1965).
4. Hoffmann, R. & Woodward, R. B. Orbital symmetries and endo-exo relationships in concerted cycloaddition reactions. J. Am. Chem. Soc. 87, 4388-4389 (1965).
5. Cookson, R. C., Drake, B. V., Hudec, J. & Morrison, A. The adduct of tropone and cyclopentadiene: A new type of cyclic reaction. Chem. Commun. 15-16 (1966).
6. Takeshita, H., Wada, Y., Mori, A. & Hatsui, T. The cycloaddition reaction of isobenzofuran with some tropones. Chem. Lett. 2, 335-336 (1973).
7. Dahnke, K. R. & Paquette, L. A. Exploratory synthetic studies involving the tricyclo[9.3.0.02, 8]tetradecane ring system peculiar to the cyathins. J. Org. Chem. 59, 885-899 (1994).
8. Li, P. & Yamamoto, H. Formal synthesis of platencin. Chem. Commun. 46, 6294-6295 (2010).
9. Li, P. & Yamamoto, H. Lewis acid catalyzed inverse-electron-demand Diels-Alder reaction of tropones. J. Am. Chem. Soc. 131, 16628-16629 (2009).
10. Houk, K. N., Luskus, L. J. & Bhacca, N. S. Novel double [6+4] cycloaddition of tropone to dimethylfulvene. J. Am. Chem. Soc. 92, 6392-6394 (1970).
11. Trost, B. M. & Seoane, P. R. [6+3] Cycloaddition to nine-membered ring carbocycles. J. Am. Chem. Soc. 109, 615-617 (1987).
12. Trost, B. M., McDougall, P. J., Hartmann, O. & Wathen, P. T. Asymmetric synthesis of bicyclo[4.3.1]decadienes and bicyclo[3.3.2]decadienes via [6+3] trimethylenemethane cycloaddition with tropones. J. Am. Chem. Soc. 130, 14960-14961 (2008).
13. Trost, B. M. & McDougall, P. J. Access to a welwitindolinone core using sequential cycloadditions. Org. Lett. 11, 3782-3785 (2009).
14. Rigby, J. H. & Fleming, M. Construction of the ingenane core using an Fe(III) or Ti(IV) Lewis acid-catalyzed intramolecular [6+4] cycloaddition. Tetrahedron Lett. 43, 8643-8646 (2002).
15. Isakovic, L., Ashenhurst, J. A. & Gleason, J. L. Application of Lewis acid catalyzed tropone [6+4] cycloadditions to the synthesis of the core of CP-225, 917. Org. Lett. 3, 4189-4192 (2001).
16. Ashenhurst, J. A. & Gleason, J. L. CP-225, 917 synthetic studies: unusual hydroboration regioselectivity influenced by remote functional groups. Tetrahedron Lett. 49, 504-507 (2008).
17. Ashenhurst, J. A., Isakovic, L. & Gleason, J. L. Application of a [6+4] cycloaddition strategy toward the total synthesis of CP-225, 917. Tetrahedron 66, 368-378 (2010).
18. Nozoe, T., Mukai, T., Osaka, K. & Shishido, N. Synthesis of some 8, 8-disubstituted heptafulvene derivatives. Bull. Chem. Soc. Jpn 34, 1384-1390 (1961).
19. Mukai, T., Tezuka, T. & Akasaki, Y. Tropone dimer. A new type of photocycloaddition reaction. J. Am. Chem. Soc. 88, 5025-5026 (1966).
20. Cantrell, T. S. Photochemical 8+2 cycloadditions of tropone. J. Am. Chem. Soc. 93, 2540-2541 (1971).
21. Rigby, J. H. et al. Metal-promoted higher-order cycloaddition reactions. Stereochemical, regiochemical, and mechanistic aspects of the [6φ+4φ] reaction. J. Am. Chem. Soc. 115, 1382-1396 (1993).
22. Xie, M. et al. Catalytic asymmetric [8+2] cycloaddition: synthesis of cycloheptatriene-fused pyrrole derivatives. Angew. Chem. Int. Ed. 52, 5604-5607 (2013).
23. Firrell, N. F. & Hickmott, P. W. Enamine chemistry. Part VI. Structure and proton magnetic resonance spectra of dienamines. J. Chem. Soc. B 293-298 (1969).
24. Firrell, N. F. & Hickmott, P. W. Enamine chemistry. Part VII. Synthesis and structure of dienamines of 3-Alkyl-5, 5-dimethylcyclohex-2-enones. Factors affecting the formation and relative stability of exo-And endo-cyclic diene systems. J. Chem. Soc. C 716-719 (1970).
25. Hayashi, R., Feltenberger, J. B. & Hsung, R. P. Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition. Org. Lett. 12, 1152-1155 (2010).
26. Xia, A.-B., Xu, D.-Q., Wu, C., Zhao, L. & Xu, Z.-Y. Organocatalytic Diels-Alder reactions catalysed by supramolecular self-Assemblies formed from chiral amines and poly(alkene glycol)s. Chem. Eur. J. 18, 1055-1059 (2012).
27. Sundén, H., Ibrahem, I., Eriksson, L. & Córdova, A. Direct catalytic enantioselective aza-Diels-Alder reactions. Angew. Chem. Int. Ed. 44, 4877-4880 (2005).
28. Xu, D.-Q. et al. In situ enamine activation in aqueous salt solutions: highly efficient asymmetric organocatalytic Diels-Alder reaction of cyclohexenones with nitroolefins. Angew. Chem. Int. Ed. 48, 3821-3824 (2009).
29. Feng, X. et al. Stereodivergence in amine-catalyzed regioselective [4+2] cycloadditions of β-substituted cyclic enones and polyconjugated malononitriles. J. Am. Chem. Soc. 134, 19942-19947 (2012).
30. Bencivenni, G., Galzerano, P., Mazzanti, A., Bartoli, G. & Melchiorre, P. Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis. Proc. Natl Acad. Sci. 107, 20642-20647 (2010).
31. Bastida, D., Liu, Y., Tian, X., Escudero-Adán, E. & Melchiorre, P. Asymmetric vinylogous aldol reaction via H-bond-directing dienamine catalysis. Org. Lett. 15, 220-223 (2013).
32. Bencivenni, G. et al. Targeting structural and stereochemical complexity by organocascade catalysis: construction of spirocyclic oxindoles having multiple stereocenters. Angew. Chem. Int. Ed. 48, 7200-7203 (2009).
33. Gu, X. et al. Direct catalytic asymmetric doubly vinylogous Michael addition of α, β-unsaturated γ-butyrolactams to dienones. Angew. Chem. Int. Ed. 54, 10249-10253 (2015).
34. Pellissier, H. Asymmetric organocatalytic cycloadditions. Tetrahedron 68, 2197-2232 (2012).
35. Mose, R., Jensen, M. E., Preegel, G. & Jørgensen, K. A. Direct access to multifunctionalized norcamphor scaffolds by asymmetric organocatalytic Diels-Alder reactions. Angew. Chem. Int. Ed. 54, 13630-13634 (2015).
36. Melchiorre, P. Cinchona-based primary amine catalysis in the asymmetric functionalization of carbonyl compounds. Angew. Chem. Int. Ed. 51, 9748-9770 (2012).
37. Oda, M., Tani, H. & Kitahara, Y. Reversible additions of an enamine to 8, 8-disubstituted heptafulvenes. J. Chem. Soc. D http://dx.doi.org/10.1039/C2969000739A (1969).
38. Kitahara, Y. & Oda, M. The Jerusalem Symposia on Quantum Chemistry and Biochemistry (eds Bergmann, E.D. & Pullman, B.) 284-295 (The Jerusalem Academy of Sciences and Humanities, 1971).
39. Mori, M., Hayamizu, A. & Kanematsu, K. Frontier-controlled cycloaddition reactions of cyclopentadienones having electron-donating or-Attracting substituents: configuration of adducts and kinetic studies. J. Chem. Soc. Perkin Trans. 1259-1272 (1981).
40. Oda, M., Funamizu, M. & Kitahara, Y. Cycloaddition reactions of tropone with enamines. J. Chem. Soc. D 737-738 (1969).
41. Lam, Y.-H. & Houk, K. N. Origins of stereoselectivity in intramolecular aldol reactions catalyzed by cinchona amines. J. Am. Chem. Soc. 137, 2116-2127 (2015).
42. Simon, A., Lam, Y.-H. & Houk, K. N. Transition states of vicinal diaminecatalyzed aldol reactions. J. Am. Chem. Soc. 138, 503-506 (2016).