An approach to highly functionalized dendrimers from chiral, non-racemic synthetic monomers

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6077-6080

  McGrath, Dominic V ^a   Wu, Mu Jen ^a   Chaudhry, Umer ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMER; MONOMER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; HYDROXYLATION; REACTION ANALYSIS; SURFACE PROPERTY; SYNTHESIS;

EID: 0030593591     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01295-6     Document Type: Article

References (25)

1. (1) Tomalia, D.A.; Naylor, A.M.; Goddard, W.A. Angew. Chem. Int. Ed. Engl. 1990, 29, 138-175.
2. (2) Fréchet, J.M.J. Science 1994, 263, 1710-1715.
3. (3) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 2413-2420.
4. (4) Mekelburger, H-B.; Jaworek, W.; Vögtle, F. Angew. Chem. Int. Ed. Engl. 1992, 31, 1570-1576.
5. (5) Newkome, G.R.; Guther, R.; Moorefield, C.N.; Cardullo, F.; Echegoyen, L.; Perez-Cordero, E.; Luftmann, H. Angew. Chem. Int. Ed. Eng. 1995, 34, 2023-6.
6. (6) Miedaner, A.; Curtis, C.J.; Barkley, R.M.; DuBois, D.L. Inorg. Chem. 1994, 33, 5482-5490.
7. (7) Knapen, J.W.J.; van der Made, A.W.; de Wilde, J.C.; van Leeuwen, P.W.N.M.; Wijkens, P.; Grove, D.M.; van Koten, G. Nature 1994, 372, 659-63.
8. (8) Newkome, G.R.; Lin, X.; Weis, C.D. Tetrahedron: Asymmetry 1991, 2, 957-960.
9. (9) Hudson, R.H.E.; Damha, MJ. J. Am. Chem. Soc. 1993, 115, 2119-2124.
10. (10) Twyman, L.J.; Beezer, A.E.; Mitchell, J.C. Tetrahedron Lett. 1994, 35, 4423-4424.
11. (11) Chapman, T.M.; Hillyer, G.L.; Mahan, E.J.; Shaffer, K.A. J. Am. Chem. Soc. 1994, 116, 11195-11196.
12. (12) Jansen, J.F.G.A.; Peerlings, H.W.I.; de Brabander-Van den Berg, E.M.M.; Meijer, E.W. Angew. Chem., Int. Ed. Eng. 1995, 34, 1206-1209.
13. (13) Jansen, J.F.G.A.; de Brabander-Van den Berg, E.M.M.; Meijer, E.W. Science 1994, 266, 1226-1229.
14. (14) (a) Chow, H.-F.; Fok, L.F.; Mak, C.C. Tetrahedron Lett. 1994, 35, 3547-3550.
15. (b) Chow, H.-F.; Mak, C.C. J. Chem. Soc., Perkin Trans. 1 1994, 2223-2228.
16. (15) (a) Murer, P.; Seebach, D. Angew. Chem. Int. Ed. Eng. 1995, 34, 2116-19.
17. (b) Seebach, D.; Lapierre, J.-M.; Dreiveldinger, G.; Skobridis, K. Helv. Chim. Acta. 1994, 77, 1673-1688.
18. (c) Seebach, D.; Lapierre, J.-M.; Skobridis, K.; Greivelkinger, G. Angew. Chem. Int. Ed. Engl. 1994, 33, 440-442.
19. (16) Chang, H.-T.; Chen; C-T.; Kondo, T.; Siuzdak, G.; Sharpless, K.B. Angew. Chem. Int. Ed. Eng. 1996, 35, 182-6.
20. (17) Brunner, H.; Altmann, S. Chem. Ber. 1994, 127, 2285-2296.
21. (18) Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev. 1994, 94, 2483-2547.
22. 13C NMR) analyses. Enantiomeric excess of the diol of 2 is >97% by chiral HPLC (Chiralcel OD, 100% EtOH) on the underivatized compound. Recrystallization of 3 (heptane) increases the optical purity to >99%.
23. (20) Hawker, C.J.; Fréchet, J.M.J. J. Am. Chem. Soc. 1990, 112, 7638-7647.
24. 3) δ 160.11 (A), 159.96 (B), 156.81 (C), 142.09 (D), 139.60 (E), 139.36 (F), 136.86 (G), 136.81 (G), 136.79 (G), 129.65 (H), 128.54 (I), 127.96 (J), 127.57 (J), 127.49 (I), 127.01 (J), 113.99 (K), 109.49 (L), 106.47 (M), 105.86 (N), 101.99 (O), 101.52 (P), 85.19 (Q), 84.87 (Q), 70.09 (R), 69.91 (S), 69.84 (T), 50.69 (U), 29.68 (V), 27.17 (W), 27.11 (W). (equation presented)
25. (22) Eliel, E.L.; Wilen, S.H. Stereochemistry of Organic Compounds; Wiley: New York, 1994.