Asymmetric Phenol Oxidation. Stereospecific and Stereoselective Oxidative Coupling of a Chiral Tetrahydronaphthol

Journal of Organic Chemistry

Volumn 46, Issue 12, 1981, Pages 2547-2557

  Feringa, Ben ^a   Wynberg, Hans ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001361497     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00325a022     Document Type: Article

References (36)

1. Partially published in a preliminary communication: B. Feringa and H. Wynberg, J. Am. Chem. Soc., 98, 3372 (1976).
2. W. I. Taylor and A. R. Battersby, Eds., “Oxidative Coupling of Phenols”, Marcel Dekker, New York, 1967;
3. H. Erdtman and C. A. Wachtmeister, “Festschift A Stoll”, Birkhauser Verlag, Basle, Switzerland, 1957, p 144;
4. D. H. R. Barton and T. Cohen, Eds., “Oxidative Coupling of Phenols”, Marcel Dekker, New York., p 117;
5. A. I. Scott, Q. Rev., Chem. Soc., 19, 1 (1965).
6. Asymmetric phenol oxidation with a chiral oxidant has recently been achieved: B. Feringa and H. Wynberg, Bioorg. Chem., 7,397 (1978).
7. T. Kametani and K. Fukumoto, Synthesis, 657 (1972).
8. J. M. Bobbitt, K. H. Weisgraber, A. S. Steinfeld, and S. G. Weiss, J. Org. Chem., 35, 2884 (1970); M. Tomita, Y. Masaki, and K. Fujitani, Chem. Phar. Bull., 16,257 (1968); J. M. Bobbitt, I. Noguchi, H. Yagi, and K. H. Weisgraber, J. Am. Chem. Soc., 93, 3551 (1971); J. M. Bobbitt, I. Noguchi, H. Yagi, and K. H. Weisgraber, J. Org. Chem., 41,845 (1976); G. G. Lyle, Synthesis., 41, 850 (1976).
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14. For a literature survey, see: R. M. Tel, Ph.D. Thesis, Groningen University, 1977, Chapter I.; R. van Est-Stammer and J. B. F. N. Engberts, Tetrahedron Lett., 3215 (1971).
15. H. Wynberg and K. Lammertsma, J. Am. Chem. Soc., 95, 7912 (1973).
16. Extended studies have been published concerning absolute configuration correlations and interpretation of ORD and CD Cotton effects of aromatic chromophores.14 The quadrant rule for the ‘Lb transition (Kuriyama and co-workers'5), the quadrant rule for the ‘La transition (De Angelis and Wildeman16), and the general helicity and sector rules (Snatzke and co-workers'7) describe the correlations for “benzylic centers of asymmetry”.
17. F. Ciardelli and P. Salvador, Eds., “Fundamental Aspects and Recent Developments in ORD and CD”, Heyden and Son Ltd., London, 1973.
18. K. Kuriyama, T. Iwata, K. Moriyama, K. Kotera, Y. Hamada, R. Mitsui, and K. Takeda, J. Chem. Soc. B. 46 (1967).
19. H. H. DeAngelis and W. C. Wildman, Tetrahedron, 25, 5099 (1969).
20. G. Snatzke, “Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry”, Heyden, London, 1967, p 208;
21. G. Snatzke, M. Ksjtär, and F. Snatzke in ref 14, Chapter 3.4;
22. G. Snatzke and F. Snatzke in ref 14, Chapter 3.5.
23. Assignments of pseudoaxial conformations are based on NMR studies. Minimalization of steric repulsion and — interactions are possible in this conformation
24. Each isomer in Scheme IV has an enantiomeric form which is not shown. The projections indicate the stereochemical relationship between the C8, Cg'-methyl groups
25. K. Mislow, Top. Stereochem., 4,1-42 (1968); K. Mislow in ref 16a, pp 153-172; K. Mislow, Ann. N. Y. Acad. Sci., 93, 457 (1962).
26. Independently, chemical correlations and configurational correlations via asymmetric synthesis and X-ray analysis were made.
27. S. F. Mason, R. H. Seal, and D. R. Roberts, Tetrahedron, 30,1671 (1974).
28. W. Hug and G. Wagniére, Tetrahedron, 28, 1241 (1972).
29. J. P. Ferris, C. B. Boye, R. C. Briner, U. Weiss, I. H. Qureshi, and N. E. Sharpless, J. Am. Chem. Soc., 93, 2963 (1971).
30. The main isomer obtained in the oxidative coupling of l,2-dimethyl-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline was assigned the cis form by Bobbitt and co-workers and Lyle. 6 On the basis of the spectroscopic and optical data of the dimer (S,S)-(+)-2a, we have to conclude that this compound has the trans form, although there is quite a similarity between our data and the data obtained by the authors cited. The clarification of this point awaits an X-ray structure determination.
31. H. Wynberg and B. Feringa, Tetrahedron, 32, 2831 (1976); P. Hobza, R. Zahradnik, B. Feringa, and H. Wynberg, submitted for publication.
32. M. Morrison and G. Bayse in “Oxidases and Related Redox Systems. Proceedings of the Second International Symposium”, T. E. King, H. S. Mason, and M. Morrison, Eds., University Park Press, Baltimore, MD, 1973, p 375.
33. S. Shibata and Y. Ogihara, Tetrahedron Lett., 1777 (1963); S. Shibata, Chem. Br., 3, 110 (1967).
34. Org. React., 2, 398 (1944)
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36. A. I. Vogel, “Practical Organic Chemistry”, 3rd ed., Longman, London, 1956, p 86.