Solution and solid-state studies of a chiral zinc- sulfonamide complex relevant to enantioselective cyclopropanations

Angewandte Chemie - International Edition

Volumn 37, Issue 8, 1998, Pages 1149-1151

  Denmark, Scott E ^a   O'Connor, Stephen P ^a   Wilson, Scott R ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Asymmetric catalysis; Cyclopropanations; Sulfonamides; Zinc

Indexed keywords

EID: 0032482059     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980504)37:8<1149::AID-ANIE1149>3.0.CO;2-F     Document Type: Article

References (22)

1. a) J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley-Interscience, New York, 1995, p. 57-67; for corresponding ligands, see
2. b) H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis, Vol. 2, VCH, Weinheim, 1993.
3. a) S. Kobayashi, H. Takahashi, M. Yoshioka, M. Ohno, Tetrahedron Lett. 1992, 33, 2575;
4. b) S. Kobayashi, H. Takahashi, M. Yoshioka, M. Ohno, M. Shibasaki, N. Imai, Tetrahedron 1995, 51, 12013.
5. M. Yoshioka, T. Kawakita, M. Ohno, Tetrahedron Lett. 1989, 30, 1657.
6. M. Ohno, M. Yoshioka, S. Kobayashi, H. Takahashi, T. Kawakita, Tetrahedron Lett. 1989, 30, 7095.
7. S. Kobayashi, M. Ohno, M. Yoshioka, T. Takahashi, T. Kawakita, Tetrahedron 1992, 48, 5691.
8. P. Knochel, R. Singer, Chem. Rev. 1993, 93, 2117.
9. M. Shibasaki, K. Uotsu, H. Sasai, Tetrahedron: Asymmetry 1995, 6, 71.
10. T. Kunieda, H. Imado, T. Ishizuka, Tetrahedron Lett. 1995, 36, 931.
11. E. J. Corey, R. Imwinkelried, S. Pikul, Y. B. Xiang, J. Am. Chem. Soc. 1989, 111, 5493.
12. E. J. Corey, C.-M. Yu, S. S. Kim, J. Am. Chem. Soc. 1989, 111, 5495.
13. E. J. Corey, S. Sarshar, J. Bordner, J. Am. Chem. Soc. 1992, 114, 7938.
14. a) S. E. Denmark, B. L. Christenson, D. M. Coe, S. P. O'Connor, Tetrahedron Lett. 1995, 36, 2215;
15. b) S. E. Denmark, B. L. Christenson, S. P. O'Connor, ibid. 1995, 36, 2219;
16. c) S. E. Denmark, S. P. O'Connor, J. Org. Chem. 1997, 62, 584;
17. d) ibid. 1997, 62, 3390.
18. 2Zn (417.89): C 40.24, H 6.75, N 6.70, S 15.34, Zn 15.65; found: C 40.39, H 6.91, N 6.66, S 14.88, Zn 15.83.
19. For a recent compilation of organozinc crystal structures, see a) P. O'Brien in Comprehensive Organometallic Chemistry II, Vol. 3 (Eds.: E. W. Abel, F. G. A Stone, G. Wilkinson), Pergamon Press, Tarrytown, 1995, chap. 4; for other sulfonamide structures in which zinc is bound to ntirogen atoms, see
20. b) S. Z. Haider, K. M. A. Malik, M. B. Hursthouse, S. Das, Acta Crystallogr. Sect. C 1984, 40, 1147;
21. c) U. Hartmann, H. Vahrenkamp, Inorg. Chem. 1991, 30, 4676.
22. -3; programs used: SHELXS-86, SHELXL-93. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-100967. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).