Facial diastereoselectivity in cationic propargylations with planar-chiral areneCr(CO) 3-substituted propargyl cations

European Journal of Organic Chemistry

Volumn , Issue 9, 2005, Pages 1823-1833

  Netz, Astrid ^a,b   Polborn, Kurt ^a   Nöth, Heinrich ^a   Müller, Thomas J J ^a,c  

^a UNIVERSITY OF MUNICH   (Germany)

^b ABBOTT GMBH AND CO KG   (Germany)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Addition reactions; Alkynes; Arenes; Chromium; Diastereoselectivity

Indexed keywords

EID: 18744408131     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400798     Document Type: Article

References (33)

1. For a recent review on stereoselective cationic propargylations, see, for example: T. J. J. Müller, Ew. J. Org. Chem. 2001, 2021-2033.
2. For excellent reviews see, for example: a) G. G. Melikyan, K. M. Nicholas, in Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim, 1995, pp. 118;
3. b) A. J. M. Caffyn, K. M. Nicholas, in Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, Vol. 12, pp. 685.
4. a) K. C. Nicolaou, W. M. Dai, Angew. Chem. 1991, 103, 1453-1481;
5. Angew. Chem. Int. Ed. Engl. 1991, 30, 1387-1416;
6. b) P. Magnus, T. Pitterna, J. Chem. Soc., Chem. Commun. 1991, 541-543;
7. c) P. Magnus, Tetrahedron 1994, 50, 1397-1418.
8. a) T. J. J. Müller, A. Netz, Organometallics 1998, 17, 3609-3614;
9. b) T. J. J. Müller, A. Netz, Tetrahedron Lett. 1999, 40, 3145-3148;
10. c) A. Netz, T. J. J. Müller, Tetrahedron 2000, 56, 4149-4155;
11. d) A. Netz, K. Polborn, T. J. J. Müller, J. Am. Chem. Soc. 2001, 123, 3441-3453.
12. S. Masamune, W. Choy, J. S. Petersen, L. R. Sita, Angew. Chem. 1985, 97, 1-31;
13. Angew. Chem. Int. Ed. Engl. 1985, 24, 1-31.
14. Calculated with PC Spartan Pro, Wavefunction Inc., 1999.
15. M. T. Reetz, M. Sauerwald, J. Organomet. Chem. 1990, 382, 121-128.
16. alpha rotation.
17. α radiation and a graphite monochromator was used for the crystallographic work and data collection. A single crystal of compound 9a was placed on a glass fiber with perfluoro ether oil and mounted on a goniometer head, which was cooled to -80°C with a Siemens LT2 device. The unit cell was determined with the program SMART from reflections collected on five sets of 15 frames each collected at five different settings of angles. Data collection was performed in the hemisphere mode at 5 s for each frame. Reflections on a total of 1360 frames were collected in the hemisphere mode of the program SMART (Bruker Analytical Instruments, Madison, Version 4.1). Data reduction was performed with the program SAINT (Bruker Analytical Instruments, Madison, Version 5.1). For structure solution and refinement the programs of SHELXTL were used. Non-hydrogen atoms were refined anisotropically. Hydrogen atoms were placed in calculated positions and included in the final refinements with a riding model.
18. CCDC-248928 (for 7a), -253713 (for 9a), and -248929 (for 17a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
19. M. Hesse, H. Meier, B. Zeeh, in Spektroskopische Methoden in der organischen Chemie, Georg Thieme Verlag, Stuttgart, New York, 4. Auflage, 1991, 105.
20. H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010;
21. Angew. Chem. Int. Ed. Engl. 1994, 33, 938-957.
22. F. A. Carey, R. F. Sundberg, in Organische Chemie- Ein weiter-führendes Lehrbuch (Eds.: H. J. Schäfer, D. Hoppe, G. Erker), Wiley-VCH, Weinheim, New York, Basel, Cambridge, Tokyo, 1st ed. (in German), 1995, p. 103 and p. 164.
23. A. Mengel, O. Reiser, Chem. Rev. 1999, 99, 1191-1223.
24. A. R. Ofial, H. Mayr, J. Org. Chem. 1996, 61, 5823-5830.
25. Various editors, Organikum, 14th edition, VEB Deutscher Verlag der Wissenschaften, Berlin, 1993.
26. [l7] a) G. Stork, P. F. Hudrlik, J. Am. Chem. Soc. 1968, 90, 4462-4464;
27. b) P. Amice, L. Blanco, J. M. Conia, Synthesis 1976, 196-197;
28. c) I. Paterson, I. Fleming, Tetrahedron Lett. 1979, 20, 995-998;
29. d) T. V. Lee, J. Toczek, Tetrahedron Lett. 1982, 23, 2917-2920;
30. e) T. V. Lee, J. O. Okonkwo, Tetrahedron Lett. 1983, 24, 323-326;
31. f) M. Bockman, D. Shukla, J. K. Kochi, J. Chem. Soc., Perkin Trans. 2 1996, 1623-1632.
32. H. O. House, L. J. Czuba, M. Gall, H. D. Olmstead, J. Org. Chem. 1968, 34, 2324-2336.
33. I. Fleming, I. Paterson, Synthesis 1979, 736-738.