Congeners of Troeger's base as chiral ligands

Tetrahedron Asymmetry

Volumn 11, Issue 14, 2000, Pages 2875-2879

  Harmata, Michael ^a   Kahraman, Mehmet ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DIAMINE; DIETHYLZINC; LIGAND; POLYCYCLIC HYDROCARBON;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034725676     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00255-X     Document Type: Article

References (15)

1. (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: Chichester, 1992; pp. 237-249.
2. (b) Bag, B. G. Curr. Sci. 1995, 68, 279.
3. (c) Demeunynck, M.; Tatibouet, A. Prog. Heterocycl. Chem. 1999, 11, 1.
4. For an example and leading references, see: Kim, E.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11192.
5. Wilen, S. H.; Qi, J. Z. J. Org. Chem. 1991, 56, 485.
6. Maitra, U.; Bag, B. G.; Rao, P.; Powell, D. J. Chem. Soc., Perkin Trans. 1 1995, 2049.
7. Harmata, M.; Carter, K. W.; Jones, D. E.; Kahraman, M. Tetrahedron Lett. 1996, 37, 6267.
8. ur-Rahman, S. J. Chem. Soc. Pak. 1987, 9, 503.
9. Goldberg, Y.; Alper, H. Tetrahedron Lett. 1995, 36, 369.
10. Xu, F.; Tillyer, R. D.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron: Asymmetry 1998, 9, 1651.
11. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
12. For some recent examples, see: (a) Legrand, O.; Brunel, J.-M.; Buono, G. Tetrahedron Lett. 2000, 41, 2105. (b) Spieler, J.; Huttenloch, O.; Waldmann, H. Eur. J. Org. Chem. 2000, 3, 391.
13. For some recent examples, see: (a) Legrand, O.; Brunel, J.-M.; Buono, G. Tetrahedron Lett. 2000, 41, 2105. (b) Spieler, J.; Huttenloch, O.; Waldmann, H. Eur. J. Org. Chem. 2000, 3, 391.
14. The dextrorotatory (+) enantiomer is listed as 5R,11R in the Fluka catalog. However, Wilen showed that the absolute configuration of the (+) isomer is actually 5S,11S. See Ref. 3.
15. Enantioselectivity was determined by formation of the corresponding acetate and analysis on a Chiraldex B-PH column or derivatization with (R)-(+)-1-phenylethyl isocyanate followed by capillary GC analysis of the resulting diastereomers.