Scalemic β-amino sulfide ligands: Use in enantioselective conjugate additions and X-ray analysis of a dimeric copper(I) complex

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2511-2514

  Cran, Graeme A ^a   Gibson, Colin L ^a   Handa, Sheetal ^b   Kennedy, Alan R ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; LIGAND; SULFATE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONJUGATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030249931     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00320-5     Document Type: Article

References (18)

1. 1. For reviews on the enantioselective conjugate addition see: (a) Leonard, J., Contemp. Org. Synth., 1994, 1, 387;
2. (b) Rossiter, B. E.; Swingle, N. M., Chem. Rev., 1992, 92, 771;
3. (c) Perlmutter P., Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, Oxford 1992.
4. 2. (a) Tanaka, K; Matsui, J.; Somemiya, K.; Suzuki, H., Synlett., 1994, 351 and references cited therein;
5. (b) Corey, E. J.; Naef, R.; Hannon, J., J. Am. Chem. Soc., 1986, 108, 7114.
6. 3. Swingle, N. M.; Reddy, K. V.; Rossiter, B. E., Tetrahedron, 1994, 50, 4455 and references cited therein.
7. 4. (a) Dieter, R. K.; Lagu, B.; Deo, N.; Dieter, J. W., Tetrahedron Lett., 1990, 31, 4105;
8. (b) Dieter, R. K.; Tokles, M., J. Am. Chem. Soc., 1987, 109, 2040;
9. (c) Ahn, K.-H.; Klassen, R. B.; Lippard, S. J., Organomet., 1990, 9, 3178;
10. (d) Bertz, S. H.; Dabbagh, G.; Sundararajan, G., J. Org. Chem., 1986, 51, 4953.
11. 5. Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G., Tetrahedron: Asymmetry, 1991, 2, 1097; Zhou, Q.-L.; Pfalz, A., Tetrahedron, 1994, 50, 4467; Zhou; Q.-L.; Pfalz, A., Tetrahedron Lett., 1993, 34, 7725.
12. 5. Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G., Tetrahedron: Asymmetry, 1991, 2, 1097; Zhou, Q.-L.; Pfalz, A., Tetrahedron, 1994, 50, 4467; Zhou; Q.-L.; Pfalz, A., Tetrahedron Lett., 1993, 34, 7725.
13. 5. Lambert, F.; Knotter, D. M.; Janssen, M. D.; van Klaveren, M.; Boersma, J.; van Koten, G., Tetrahedron: Asymmetry, 1991, 2, 1097; Zhou, Q.-L.; Pfalz, A., Tetrahedron, 1994, 50, 4467; Zhou; Q.-L.; Pfalz, A., Tetrahedron Lett., 1993, 34, 7725.
14. 6. Dymock, B.; Gibson, C. L., Unpublished results.
15. 7. Cran, G. A.; Gibson, C. L.; Handa, S., Tetrahedron: Asymmetry, 1995, 6, 1553.
16. -3. The absolute configuration of the structure was obtained by examining the anomalous scattering of Friedel mates and was confirmed by obtaining significantly better R factors for the given enantiomer. Selected bond lengths (Å), bond angles (°) and torsion angles (°): I(2)-Cu(2) 2.636(1), I(2)-Cu(2*) 2.575(1), Cu(2)-Cu(2*) 2.650(2), Cu(2)-S(2) 2.325(2), Cu(2)-N(2), 2.158(8), I(2)-Cu(2)-I(2*) 117.47(3), I(2)-Cu(2)-S(2) 108.55(7), I(2)-Cu(2)-N(2) 105.6(2), I(2*)-Cu(2)-S(2) 125.57(8), I(2*)-Cu(2)-N(2) 106.7(2), S(2)-Cu(2)-N(2) 86.1(2), I(2)-Cu(2)-I(2*)-Cu(2*) 13.33(8), Cu(2)-I(2)-Cu(2*)-S(2*) -131.02(8) Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.
17. 9. Fuller, M. W.; Costanzo, V.; Murray, K. S.; Black, D. St.C.; Hambley, T. W.; Snow, M. R., Aus. J. Chem., 1985, 38, 865; Stoffels, A. L. E.; Haanstra, W. G.; Driessen, W. L.; Reedijk, J., Angew. Chem. Int. Ed. Engl., 1990, 29, 1419.
18. 9. Fuller, M. W.; Costanzo, V.; Murray, K. S.; Black, D. St.C.; Hambley, T. W.; Snow, M. R., Aus. J. Chem., 1985, 38, 865; Stoffels, A. L. E.; Haanstra, W. G.; Driessen, W. L.; Reedijk, J., Angew. Chem. Int. Ed. Engl., 1990, 29, 1419.