1 / 20

Diels-Alder in Aqueous Molecular Hosts: Unusual Regioselectivity and Efficient Catalysis

Diels-Alder in Aqueous Molecular Hosts: Unusual Regioselectivity and Efficient Catalysis Michito Yoshizawa, Masazumi Tamura, Makoto Fujita* Science 2006 , 312 , 251-254. Diels-Alder Reaction. Rebek J. et al. Nature 1997 , 385 , 50-52. Epoxidation. Angew. Chem. Int. Ed. Engl.

steel-joseph
Download Presentation

Diels-Alder in Aqueous Molecular Hosts: Unusual Regioselectivity and Efficient Catalysis

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Diels-Alder in Aqueous Molecular Hosts: Unusual Regioselectivity and Efficient Catalysis Michito Yoshizawa, Masazumi Tamura, Makoto Fujita* Science2006, 312, 251-254.

  2. Diels-Alder Reaction Rebek J. et al. Nature1997, 385, 50-52.

  3. Epoxidation Angew. Chem. Int. Ed. Engl. 2001, 40, 4239-4242.

  4. aza-Cope rearrangement Fe Angew. Chem. Int. Ed. Engl. 2004, 43, 6748-6751.

  5. Regioselective cycloaddition Org. Lett. 2002, 4, 327-329.

  6. Diels-Alder Reaction anthracenes phthalimides 1 9 10 4 Barrier (kJ mol-1) 3a 79.4 3b 49.8 ΔE = 29.6 Chem. Phys. Lett.2003, 368, 630-638.

  7. B-ring A-ring J. Am. Chem. Soc. 1965, 87, 4649-4651 .

  8. H2O 70 oC 1’ Nature 1995, 378, 469-471. J. Am. Chem. Soc. 2004, 126, 6846-6847.

  9. Angew. Chem. Int. Ed. Engl. 2001, 40, 1879-1884.

  10. Cyclic siloxane formation RSi(OMe)3 J. Am. Chem. Soc. 2001, 123, 10454-10459

  11. Td 5 hr C3v

  12. Syn-1,4-Diels-Alder adduct (5) Yield : > 98 % No other : 1,9-adduct or anti-1,4-adduct without 1 9 ,10-Diels-Alder adduct 44 %

  13. π-π stacking interaction (3.3 Å)

  14. (10 mmol%) 5 hr > 99 %

  15. aromatic-aromatic or charge-transfer interactions the encapsulated product is considerably destabilized and smoothly replaced by incoming reagents the host-guest aromatic stacking interaction

More Related