Unprecedented encapsulation of carbonyl guest with designer Lewis acid receptor

Angewandte Chemie - International Edition

Volumn 37, Issue 21, 1998, Pages 3039-3041

  Ooi, Takashi ^a   Kondo, Yuichiro ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Alkylations; Aluminum; Cage compounds; Cyclodditions; Lewis acids

Indexed keywords

ACID; CARBONYL DERIVATIVE; PIPERAZINE DERIVATIVE; RECEPTOR;

ALKYLATION; ARTICLE; ENCAPSULATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0032538778     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981116)37:21<3039::AID-ANIE3039>3.0.CO;2-9     Document Type: Article

References (23)

1. D. J. Cram, Nature 1992, 356, 29.
2. R. C. Helgeson, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1997, 119, 3229.
3. J.-M. Lehn, Angew. Chem. 1988, 100, 92;
4. Angew. Chem. Int. Ed. Engl. 1988, 27, 89.
5. V. T. D'Souza, M. T. Bender, Acc. Chem. Res. 1987, 20, 146.
6. R. Arad-Yellin, B. S. Green, Nature 1994, 371, 320.
7. B.-H. Huisman, D. M. Rudkevich, F. C. J. M. van Veggel, D. N. Reinhoudt, J. Am. Chem. Soc. 1996, 118, 3523.
8. R. M. Grotzfeld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487, and references therein.
9. a) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131;
10. b) K. Maruoka, I. Shimada, H. Imoto, H. Yamamoto, Synlett 1994, 519;
11. c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091;
12. d) S. Saito, H. Yamamoto, J. Org. Chem. 1996, 67, 2928;
13. e) T. Ooi, Y. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230;
14. Angew. Chem. Int. Ed. Engl. 1997, 36, 1181;
15. f) T. Ooi, Y. Kondo, K. Maruoka, Angew. Chem. 1997, 109, 1231;
16. Angew. Chem. Int. Ed. Engl. 1997, 36, 1183.
17. w. = 0.063. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-103289. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
18. Although the relative binding strengths of the guests studied here have not been established precisely, it may be predicted based on our previous observation on the binding priority of various oxygen-containing substrates with a Lewis acidic bulky organoaluminum reagent (K. Maruoka, S. Nagahara, H. Yamamoto, Tetrahedron Lett. 1990, 31, 5475.)
19. The concentration of the substrate was 0.0625 M in each case.
20. For recent beautiful demonstration, see: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50.
21. See also: C. J. Walter, K. M. Sanders, Angew. Chem. 1995, 107, 223;
22. Angew. Chem. Int. Ed. Engl. 1995, 34, 217;
23. D. Philp, A. Robertson, Chem. Commun. 1998, 879.