Diastereoselective benzylic arylation of tetralins

Chemistry - A European Journal

Volumn 16, Issue 1, 2010, Pages 50-54

  Davoust, Marion ^a   Kitching, Jacki A ^a   Fleming, Matthew J ^b   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b SOLVIAS AG   (Switzerland)

Author keywords

Alkylation; Benzylic alcohols; Carbocations; Diastereoselectivity; Electrophilic aromatic substitution

Indexed keywords

BENZYLIC ALCOHOLS; CARBOCATIONS; DIASTEREO-SELECTIVITY; ELECTROPHILIC AROMATIC SUBSTITUTION; ELECTROPHILIC AROMATIC SUBSTITUTIONS;

ALKYLATION; AROMATIC HYDROCARBONS; SUBSTRATES;

STEREOSELECTIVITY;

BENZYL DERIVATIVE; TETRALIN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

BENZYL COMPOUNDS; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM; TETRAHYDRONAPHTHALENES;

EID: 73949122198     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902694     Document Type: Article

References (26)

1. a) K. Mertins, I. Iovel, J. Kischel, A. Zapf, M. Beller, Angew. Chem. 2005, 117, 242
2. Angew. Chem. Int. Ed. 2005, 44, 238
3. b) I. Iovel, K. Mertins, J. Kischel, A. Zapf, M. Beller, Angew. Chem. 2005, 117, 3981
4. Angew. Chem. Int. Ed. 2005, 44, 3913
5. c) K. Mertins, I. Iovel, J. Kischel, A. Zapf, M. Beller, Adv. Synth. Catal. 2006, 348, 691
6. d) M. Rueping, B. J. Nachtsheim, W. Ieawsuwan, Adv. Synth. Catal. 2006, 348, 1033
7. e) X. Deng, J. T. Liang, J. Liu, H. McAllister, C. Schubert, N. S. Mani, Org. Process Res. Dev. 2007, 11, 1043.
8. a) F. Mühlthau, O. Schuster, T. Bach, J. Am. Chem. Soc. 2005, 127, 9348
9. b) F. Mühlthau, D. Stadler, A. Goeppert, G. A. Olah, G. K. Surya Prakash, T. Bach, J. Am. Chem. Soc. 2006, 128, 9668
10. c) D. Stadler, F. Mühlthau, P. Rubenbauer, E. Herdtweck, T. Bach, Synlett 2006, 2573
11. d) D. Stadler, T. Bach, Chem. Asian J. 2008, 3, 272
12. e) P. Rubenbauer, T. Bach, Adv. Synth. Catal. 2008, 350, 1125
13. f) J. Y. L. Chung, D. Mancheno, P. G. Dormer, N. Variankaval, R. G. Ball, N. N. Tsou, Org. Lett. 2008, 10, 3037
14. g) F. Effenberger, T. Weber, Angew. Chem. 1987, 99, 146
15. Angew. Chem. Int. Ed. Engl. 1987, 26, 142
16. h) K. Suzuki, T. Tatsuoka, T. Ishihara, T. Ohno, K. Aisaka, R. Ogino, M. Kuroki, F. Satoh, S. Miyano, K. Sumoto, Chem. Pharm. Bull. 1996, 44, 132
17. i) W. L. Bencze, L. I. Barsky, R.W.J. Carney, A. A. Renzi, G. deStevens, J. Med. Chem. 1967, 10, 138.
18. a) W. K. Brewster, D. E. Nichols, R. M. Riggs, D. M. Mottola, T. W. Lovenberg, M. H. Lewis, R. B. Mailman, J. Med. Chem. 1990, 33, 1756
19. b) T. W. Lovenberg, W. K. Brewster, D. M. Mottola, R. C. Lee, R. M. Riggs, D. E. Nichols, M. H. Lewis, R. B. Mailman, Eur. J. Pharmacol. 1989, 166, 111
20. c) L. Shao, F. Wang, S. C. Malcolm, M. C. Hewitt, L.R. Bush, M. Varney, U. Campbell, S. R. Engel, L. W. Hardy, P. Koch, J. Ma (Sepracor Inc.), WO 2007081542A2, 2007
21. d) M. R. Michaelides, Y. Hong (Abbott Laboratories), US 5597832A, 1997
22. e) J. G. Berger, W. K. Chang, J. W. Clader, D. Hou, R. E. Chipkin, A. T. McPhail, J. Med. Chem. 1989, 32, 1913
23. f) W.-L. Wu, D. A. Burnett, R. Spring, W. J. Greenlee, M. Smith, L. Favreau, A. Fawzi, H. Zhang, J. E. Lachowicz, J. Med. Chem. 2005, 48, 680.
24. For a review, see: M. Lautens, K. Fagnou, S. Hiebert, Acc. Chem. Res. 2003, 36, 48.
25. a) M. Fleming, M. Lautens, unpublished results
26. b) S. Hagishita, M. Shiro, K. Kuriyama, J. Chem. Soc. Perkin Trans. 1 1984, 1655.