1. Diels-Alder in Aqueous Molecular Hosts:
Unusual Regioselectivity and Efficient Catalysis
Michito Yoshizawa, Masazumi Tamura, Makoto Fujita*
Science 2006, 312,

2. Diels-Alder Reaction
Rebek J. et al. Nature 1997, 385,

3. Epoxidation
Angew. Chem. Int. Ed. Engl.
2001, 40,

4. aza-Cope rearrangementFe
Angew. Chem. Int. Ed. Engl.
2004, 43,

5. Regioselective cycloaddition
Org. Lett. 2002, 4,

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

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

9. H2O
70 oC 1’
Nature 1995, 378,
J. Am. Chem. Soc. 2004, 126,

10. Angew. Chem. Int. Ed. Engl. 2001, 40,

11. Cyclic siloxane formation
RSi(OMe)3
J. Am. Chem. Soc. 2001, 123,

13. Td
5 hr
C3v

14. 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 %

15. π-π stacking interaction
(3.3 Å)

18. (10 mmol%)
5 hr
> 99 %

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