Asymmetric induction in the nucleophile addition to η6-arene-tricarbonyl-chromium(0) complexes

Tetrahedron Letters

Volumn 37, Issue 18, 1996, Pages 3089-3092

  Semmelhack, M F ^a   Schmalz, Hans Günther ^a,b  

^a PRINCETON UNIVERSITY   (United States)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029976129     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00572-2     Document Type: Article

References (19)

1. (a) M. F. Semmelhack, J. J. Harrison, Y. Thebtaranonth, J. Org. Chem., 44, 3275 (1979);
2. (b) M. F. Semmelhack, H. T. Hall, Jr., R. Farina, M. Yoshifuji, G. Clark, T. Bargar, K. Hirotsu, and J. Clardy, J. Am. Chem. Soc., 101, 3535 (1979);
3. (c) M. F. Semmelhack, G. R. Clark, T. Bargar, J. L. Garcia, J. J. Harrison, Y. Thebtaranonth, W. Wulff, and A. Yamashita, Tetrahedron, 37, 3957 (1981);
4. d. M. F. Semmelhack in "Comprehensive Organometallic Chemistry II", E. W. Abel, F. G. A. Stone, and G Wilkenson, eds., Vol 12, Pergamon Press, NY, 1995. p 979.
5. For a review of this general process, see: M. F. Semmelhack in "Comprehensive Organic Synthesis," B. M. Trost and I. Fleming, eds.; Vol 4, Pergamon Press, Oxford, 1992, p 521ff. See also reference 1d.
6. (a) Pearson, A. J.; Zhu, P. Y.; Youngs, W. J.; Bradshaw, J. D.; McConville, D. M. J. Am. Chem. Soc., 1993, 115, 10376;
7. (b) Pearson, A. J.; Milletti, M. C.; Zhu, P. Y. Chem. Comm., 1995, 853.
8. Complex 6 (mp 122 - 123°C) was prepared in 91 % yield according to the procedure of Mahaffy, C. A. L.; Pauson, P. L.,Inorg. Synth., 1979, 19, 154.
9. Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc., 1975, 97, 6908.
10. Quinkert, G.; Schmalz, H. - G.; Dzierzynski, E. M.; Dürner, G.; Bats, J. W. Angew. Chem., 1986, 98, 1023.
11. Whitesell, J. K.; Liu, C. - L.; Buchanan, C. M.; Chen, H.-H.; Minton, M. A. J. Org. Chem., 1986, 51, 551.
12. -1. MS: m/e 444.0 (M+). Anal, calc.: C 67.55 %, H 6.35 %; found: C 67.61 %, H 6.43 %.
13. 13C NMR, MS and elemental analysis.
14. 3.
15. -1. MS: m/e 165.0(M+). Anal. calc.: C 72.69 % , H 9.15 %; found: C 72.42 %, H 9.16 %.
16. Kirk, D. N. Tetrahedron, 1986, 42, 777 and references cited therein.
17. We thank Prof. Nakanishi and Dr. Chang Mayland from Columbia University for recording the CD-spectrum of compound 11.
18. Kündig, E. P.; Desobry, V.; Simmons, D. P.; Wenger, E. J. Am. Chem. Soc., 1989, 111, 1804.
19. 16