Enantiomerically pure cyclic trans-1,2-diols, diamines, and amino alcohols by intramolecular pinacol coupling of planar chiral mono-Cr(CO)3 complexes of biaryls

Angewandte Chemie - International Edition

Volumn 38, Issue 9, 1999, Pages 1232-1235

  Taniguchi, Nobukazu ^b   Hata, Takeshi ^b   Uemura, Motokazu ^b  

^a Osaka Prefecture University   (Japan)

^b NONE

Author keywords

Arene complexes; Chirality; Chromium; Pinacol coupling; Samarium

Indexed keywords

AMINOALCOHOL; CHROMIUM DERIVATIVE; DIAMINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033519208     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990503)38:9<1232::AID-ANIE1232>3.0.CO;2-E     Document Type: Article

References (26)

1. a) K. Tomioka, Synthesis 1990, 541-549;
2. b) J. K. Whitesell, Chem. Rev. 1989, 89, 1581-1590;
3. c) A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517-547;
4. Angew. Chem. Int. Ed. Engl. 1994, 33, 497-526;
5. d) H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547;
6. e) D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772;
7. Angew. Chem. Int. Ed. 1998, 37, 2580-2667.
8. a) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338;
9. b) J. A. Sonderquist, Aldrichimica Acta 1991, 24, 15-23;
10. c) H. B. Kagan, J. L. Namy, Tetrahedron 1986, 42, 6573-6614;
11. d) J. L. Namy, J. Souppe, H. B. Kagan, Tetrahedron Lett. 1983, 24, 765-766.
12. K. Kamikawa, T. Watanabe, M. Uemura, J. Org. Chem. 1996, 61, 1375-1384.
13. Optically pure tricarbonylchromium complexes of o-bromobenzaldehyde and 2-bromo-3-methoxybenzaldehyde were prepared according to the following procedure: J. W. Han, S. U. Son, Y. K. Chung, J. Org. Chem. 1997, 62, 8264-8267;
14. L. A. Bromley, S. G. Davies, C. L. Goodfellow, Tetrahedron: Asymmetry 1991, 2, 139-156.
15. 3 complexes of benzaldehydes and benzaldimines, see N. Taniguchi, N. Kaneta, M. Uemura, J. Org. Chem. 1996, 61, 6088-6089;
16. N. Taniguchi, M. Uemura, Synlett 1997, 51-53.
17. 2 = H, X = NPh). 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).
18. 2 = H) was prepared by an asymmetric dihydroxylation and subsequent intramolecular biaryl coupling of trans-2,2′-dibromostilbene with 86% ee: T. R. Kelly, Q. Lin, V. Bhushan, Tetrahedron Lett. 1990, 31, 161-164.
19. a) D. S. Hays, G. C. Fu, J. Am. Chem. Soc. 1995, 117, 7283-7284;
20. b) T. Naito, K. Tajiri, T. Harimoto, I. Ninomiya, T. Kiguchi, Tetrahedron Lett. 1994, 35, 2205-2206;
21. c) T. Kiguchi, K. Tajiri, I. Ninomiya, T. Naito, Tetrahedron Lett. 1995, 36, 253-256;
22. d) J. L. Chiara, W. Cabri, S. Hanessian, Tetrahedron Lett. 1991, 32, 1125-1128;
23. e) J. P. Guidot, T. Le Gall, C. Mioskowski, Tetrahedron Lett. 1994, 35, 6671-6672.
24. K. Ohmori, M. Kitamura, K. Suzuki, Angew. Chem. 1999, 111, 1304-1307;
25. Angew. Chem. Int. Ed. 1999, 38, 1226-1229.
26. 2 = H, X = NPh) was obtained from 1 and aniline.