Synthesis of hydroquinone-, biphenol-, and binaphthol-containing aza macroheterocycles via regioselective hydroformylation and reductive amination

Tetrahedron

Volumn 59, Issue 41, 2003, Pages 8265-8274

  Angelovski, Goran ^a   Eilbracht, Peter ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

BINOL; Chiral ligands; Hydroaminomethylation; Macrocycles; Reductive amination; Regioselective hydroformylation; Rhodium catalysis

Indexed keywords

1,4 BIS(PENT 4 ENYLOXY)BENZENE; 10,15 DIBENZYL 6,7,8,9,10,11,12,13,14,15,16,17,18,19 TETRADECAHYDRO 5,20 DIOXA 10,15 DIAZADIBENZO[A,C]CYCLOEICOSENE; 10,15 DIBENZYL 6,7,8,9,10,11,12,13,14,15,16,17,18,19 TETRADECAHYDRO 5,20 DIOXA 10,15 DIAZADINAPHTHO[A,C]CYCLOEICOSENE; 10,15 DIBENZYL 7,18 DIMETHYL 6,7,8,9,10,11,12,13,14,15,16,17,18,19 TETRADECAHYDRO 5,20 DIOXA 10,15 DIAZADIBENZO[A,C]CYCLOEICOSENE; 10,15 DIBENZYL 7,18 DIMETHYL 6,7,8,9,10,11,12,13,14,15,16,17,18,19 TETRADECAHYDRO 5,20 DIOXA 10,15 DIAZADINAPHTHO[A,C]CYCLOEICOSENE; 10,17 DIBENZYL 6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21 HEXADECAHYDRO 5,22 DIOXA 10,17 DIAZADIBENZO[A,C]CYCLODOCOSENE; 10,17 DIBENZYL 6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21 HEXADECAHYDRO 5,22 DIOXA 10,17 DIAZADINAPHTHO[A,C]CYCLODOCOSENE; 10,17 DIBENZYL 7,20 DIMETHYL 6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21 HEXADECAHYDRO 5,22 DIOXA 10,17 DIAZADIBENZO[A,C]CYCLODOCOSENE; 10,17 DIBENZYL 7,20 DIMETHYL 6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21 HEXADECAHYDRO 5,22 DIOXA 10,17 DIAZADINAPHTHO[A,C]CYCLODOCOSENE; 2,2' BIS(HEX 5 ENYLOXY)[1,1']BINAPHTHALENYL; 2,2' BIS(METHYLOXY)BIPHENYL; 3 METHYL 4 [2' (2 METHYL 4 OXOBUTOXY)[1,1']BINAPHTHALENYL 2 YLOXY]BUTYRALDEHYDE; 4 [2' (4 OXOBUTOXY)BIPHENYL 2 YLOXY]BUTYRALDEHYDE; 4 [2' (4 OXOBUTOXY)[1,1']BINAPHTHALENYL 2 YLOXY]BUTYRALDEHYDE; 4 [4 (4 OXOBUTOXY)PHENOXYL]BUTYRALDEHYDE; 6 [4 (6 OXOHEXYLOXY)PHENOXY]HEXANAL; 7 [2' (7 OXOHEPTYLOXY)[1,1']BINAPHTHALENYL 2 YLOXY]HEPTANAL; 7,12 DIBENZYL 2,17 DIOXA 7,12 DIAZABICYCLO[16.2.2]DOCOSA 1(21),18(22),19 TRIENE; 7,12 DIBENZYL 4,15 DIMETHYL 2,17 DIOXA 7,12 DIAZABICYCLO[16.2.2]DOCOSA 1(21),18(22),19 TRIENE; 7,14 DIBENZYL 2,19 DIOXA 7,14 DIAZABICYCLO[18.2.2]TETRACOSA 1(23),20(24),21 TRIENE; 7,14 DIBENZYL 4,17 DIMETHYL 2,19 DIOXA 7,14 DIAZABICYCLO[18.2.2]TETRACOSA 1(23),20(24),21 TRIENE; ALDEHYDE DERIVATIVE; ALKADIENE; DIAMINE; ETHER DERIVATIVE; HYDROQUINONE DERIVATIVE; NAPHTHOL DERIVATIVE; PHENOL DERIVATIVE; RHODIUM COMPLEX; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 0141570869     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.012     Document Type: Article

References (27)

1. Zhang X.X., Bradshaw J.S., Izatt R.M. Chem. Rev. 97:1997;3313-3361.
2. Pu L. Chem. Rev. 98:1998;2405-2494.
3. Yan Y.-Y., Widhalm M. Tetrahedron: Asymmetry. 9:1998;3607-3610.
4. Krakowiak K.E., Izatt R.M., Bradshaw J.S. J. Heterocycl. Chem. 2001;1239-1248.
5. Richman J.E., Atkins T.J. J. Am. Chem. Soc. 96:1974;2268-2270.
6. (a) Armstrong L.G., Lindoy L.F. Inorg. Chem. 14:1975;1322-1326
7. (b) Lindoy L.F., Lip H.C., Power L.F., Rea J.H. Inorg. Chem. 15:1976;1724-1727
8. (c) Armstrong L.G., Grimsley P.G., Lindoy L.F., Lip H.C., Norris V.A., Smith R. J. Inorg. Chem. 17:1978;2350-2352.
9. Eilbracht P., Bärfacker L., Buss C., Hollmann C., Kitsos-Rzychon B.E., Kranemann C.L., Rische T., Roggenbuck R., Schmidt A. Chem. Rev. 99:1999;3329-3365.
10. (a) Kranemann C.L., Eilbracht P. Eur. J. Org. Chem. 2000;2367-2377
11. (b) Kranemann C.L., Costisella B., Eilbracht P. Tetrahedron Lett. 40:1999;7773-7776.
12. Pruett R.L. Adv. Organomet. Chem. 17:1979;1-60.
13. (a) Devinsky F., Lacko I., Krasnec L. Synthesis. 1980;303-305
14. (b) Bhuniya D., Singh V.K. Synth. Commun. 24:1994;375-385.
15. (a) Cuny G.D., Buchwald S.L. J. Am. Chem. Soc. 115:1993;2066-2068
16. (b) Moasser B., Gladfelter W.L. Organometallics. 14:1995;3832-3838.
17. (a) van der Veen L.A., Keeven P.H., Schoemaker G.C., Reek J.N.H., Kamer P.C.J., van Leeuwen P.W.N.M., Lutz M., Spek A.L. Organometallics. 19:2000;872-883
18. (b) Kranenburg M., van der Burgt Y.E.M., Kamer P.C.J., van Leeuwen P.W.N.M., Goubitz K., Fraanje J. Organometallics. 14:1995;3081-3089.
19. Kranemann C.L., Eilbracht P. Synthesis. 1998;71-77.
20. (a) Joseph B., Chapellier V., Mérour J.-Y., Léonce S. Heterocycles. 48:1998;1423-1430
21. (b) Mouadibb A., Joseph B., Hasnaoui A., Mérour J.-Y., Léonce S. Heterocycles. 51:1999;2127-2137
22. (c) Dinsmore C.J., Bergman J.M. J. Org. Chem. 63:1998;4131-4134
23. (d) Rocaboy C., Bauer W., Gladysz J.A. Eur. J. Org. Chem. 2000;2621-2628.
24. (a) Roffia P., Conti F., Gregorio G., Pregaglia G.F. J. Organomet. Chem. 54:1973;357-360
25. (b) Wang Z.-M., Shen M. J. Org. Chem. 63:1998;1414-1418.
26. Nakamura Y., Hollenstein R., Zsindely J., Schmid H., Oberhänsli W.E. Helv. Chim. Acta. 58:1975;1949-1977.
27. Pearson D.P.J., Leigh S.J., Sutherland I.O. J. Soc. Chem. Perkin Trans. 1. 1979;3113-3126.