Diastereoselective Friedel-Crafts alkylation reactions employing chiral cation precursors with polar α-substituents

Synlett

Volumn , Issue 16, 2006, Pages 2573-2576

  Stadler, Daniel ^a   Mühlthau, Friedrich ^a   Rubenbauer, Philipp ^a   Herdtweck, Eberhardt ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Alkylations; Carbocations; Diastereoselectivity; Electrophilic aromatic substitutions; Stereoselective synthesis

Indexed keywords

ALCOHOL; CATION; EPOXIDE; LEWIS ACID;

ARTICLE; CATALYSIS; CHIRALITY; FRIEDEL CRAFTS REACTION; STEREOCHEMISTRY;

EID: 33750067707     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951471     Document Type: Article

References (31)

1. (a) Olah, G. A.; Krishnamurti, G. A.; Prakash, G. K. S. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991, 293.
2. (b) Olah, G. A. Friedel-Crafts Chemistry; John Wiley & Sons: New York, 1973.
3. (c) Friedel-Crafts and Related Reactions, Vol. 2; Olah, G. A., Ed.; Interscience Publishers: New York, 1963.
4. (a) Price, C. C.; Lund, M. J. Am. Chem. Soc. 1940, 62, 3105.
5. (b) Streitwieser, A. Jr.; Stang, P. J. J. Am. Chem. Soc. 1965, 87, 4953.
6. (a) Mühlthau, F.; Schuster, O.; Bach, T. J. Am. Chem. Soc. 2005, 127, 9348.
7. (b) Mühlthau, F.; Stadler, D.; Goeppert, A.; Olah, G. A.; Prakash, G. K. S.; Bach, T. J. Am. Chem. Soc. 2006, 128, 9668-9675.
8. For an early example possibly involving cations related to 2, see: Hodge, E. B. J. Am. Chem. Soc. 1951, 73, 2341.
9. Alcohol 5: (a) Desai, U. V.; Pore, D. M.; Mane, R. B.; Solabannavar, S. B.; Wadgaonkar, P. P. Synth. Commun. 2004, 34, 19.
10. (b) Dumez, E.; Faure, R.; Dulcère, J.-P. Eur. J. Org. Chem. 2001, 2557.
11. Alcohol 6: (a) Das, B.; Banerjee, J.; Majhi, A.; Mahender, G. Tetrahedron Lett. 2004, 45, 9225.
12. (b) Zhong, B.; Lu, X.; Silverman, R. B. Bioorg. Med. Chem. 1998, 6, 2405.
13. Mohan, R. S.; Whalen, D. L. J. Org. Chem. 1993, 58, 2663.
14. 5S (414.5): C, 60.85; H, 5.35; N, 6.76; S, 7.74. Found: C, 60.77; H, 5.20; N, 6.74; S, 7.65.
15. 2S (262.4): C, 68.67; H, 6.92. Found: C, 68.63; H, 6.92.
16. 3-promoted reaction 7 → 9ca, in which the trans/cis ratio of the epoxide 7 varied from <5:95 to >95:5 while the product selectivity (dr = 88:12) remained constant.
17. int, = 0.038), number of observations [>2σ (I)] 3296, parameters 351. Crystallographic data (excluding structure factors) for 9ac have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-604901.
18. int = 0.053), number of observations [>2σ (I)] 6128, parameters 584. Crystallographic data (excluding structure factors) for 9ca have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-604902.
19. The sequence included (a) reduction to the aldehyde [DIBAL-H, -78 °C → r.t. (THF), 69%]
20. 2O), 76%], and
21. 3,130 °C (PhCl), 53% (two steps)].
22. Iwasawa, N.; Matsuo, T.; Iwamoto, M.; Ikeno, T. J. Am. Chem. Soc. 1998, 120, 3903.
23. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994.
24. 2 (entries 7 and 8 in Table 1).
25. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
26. 3: (a) Review: Iovel, I.; Mertins, K.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem. Int. Ed. 2005, 44, 3913.
27. (b) Kischel, J.; Jovel, I.; Mertins, K.; Zapf, A.; Beller, M. Org. Lett. 2006, 8, 19 .
28. 3: (c) Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. J. Org. Chem. 1997, 62, 6997.
29. (d) Noji, M.; Ohno, T.; Fuji, K.; Futaba, N.; Tajima, H.; Ishii, K. J. Org. Chem. 2003, 68, 9340.
30. 3: Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705.
31. 2O, 7:3) yielded the product 9ca (88.0 mg, 0.34 mmol, 67%) in a diastereomeric ratio of threat erythro 87:13.