Multifunctionalized glycolurils

Organic Letters

Volumn 1, Issue 1, 1999, Pages 39-42

  Pryor, Kent E ^a,b   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001822141     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990536t     Document Type: Article

References (21)

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2. Wang, A.; Bassett, D. U.S. Patent 4,310,450, 1982.
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5. (a) Dave, P. R.; Forohar, F.; Kaselj, M.; Gilardi, R.; Trivedi, N. Tetrahedron Lett. 1999, 40, 447.
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9. (e) Coolen, H. K. A. C.; van Leeuwen, P. W. N. M.; Nolte, R. J. M. J. Org. Chem. 1996, 61, 4739.
10. (f) Sijbesma, R. P.; Nolte, R. J. M. Top. Curr. Chem. 1995, 175, 25.
11. (a) Meissner, R.; Rebek, J., Jr.; de Mendoza, J. Science 1995, 270, 1485.
12. (b) Valdez, C.; Spitz, U. P.; Toledo, L. M.; Kubik, S. W.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 12733.
13. Pryor, K. E.; Shipps, G. W., Jr.; Skyler, D. A.; Rebek, J., Jr. Tetrahedron 1998, 54, 4107 and references therein.
14. Somin, I. N.; Kuznetsov, S. G. Khim. Nauka I Prom. 1959, 4, 801.
15. Previously reported in Kotani, T.; Ishii, A.; Nhagaki, Y.; Toyomaki, Y.; Yago, H.; Suehiro, S.; Okukado, N.; Okamoto, K. Chem. Pharm. Bull. 1997, 45, 297.
16. Substituted benzils have also been used to incorporate additional functional groups in the core molecules; see Supporting Information for an example.
17. This is thought to be the result of the production of intermediate 12, which, particularly under acidic conditions, reacts with a second equivalent of benzyl hydantoate 8 to preferentially form the cis-isomer. (equation presented)
18. Similar methodology can be applied to other polyacid glycoluril core molecules, as described in the Supporting Information.
19. Mass spectroscopy of libraries formed by the reaction of the glycoluril core with aniline and several other single amines showed that all three masses expected for the two homo-and the heterosubstituted products were present.
20. tBu-HCl under the action of DPPA is described in the Supporting Information. In this and a few other cases (with other cores, amines, and coupling reagents), the reaction was sufficiently clean to allow nonchromatographic workup.
21. Diethyl ester 18 is prepared in a manner similar to that of dibenzyl ester 7, with the substitution of ethyl bromoacetate as the alkylating agent. The dibenzyl ester should be able to be used interchangeably in this reaction.