Syntheses and Vanadium Complex of Salen-like Bissulfoximines

Synlett

Volumn 1996, Issue 8, 1996, Pages 775-776

  Bolm, Carsten ^a,b   Bienewald, Frank ^a   Harms, Klaus ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002716122     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5512     Document Type: Article

References (31)

1. Hobday, M.D.; Smith, T.D. Coord. Chem. Rev. 1972, 9, 311.
2. Srinivasan, K.; Michaud, P.; Kochi, J.K. J. Am. Chem. Soc. 1986, 108, 2309.
3. a) Noyori, R. Asymmetric Catalysis In Organic Synthesis; Wiley: New York, 1994.
4. b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
5. a) Jacobsen, E.N. In ref. 4b, p. 159.
6. b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189.
7. a) Nakajima, K.; Kojima, K.; Kojima, M.; Fujita, J. Bull. Chem. Soc. Jpn. 1990, 63, 2620.
8. b) Sasaki, C.; Nakajima, K.; Kojima, M.; Fujita, J. Ibid. 1991, 64, 1318.
9. c) Palucki, M.; Hanson, P.; Jacobsen, E.N. Tetrahedron Lett. 1992, 33, 7111.
10. d) Noda, K.; Hosoya, N.; Yanai, K.; Irie, R.; Katsuki, T. Ibid. 1994, 35, 1887.
11. e) Martínez, L.E.; Leighton, J.L.; Carsten, D.H.; Jacobsen, E.N. J. Am. Chem. Soc. 1995, 117, 5897.
12. f) Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515 and references therein.
13. Norrby, P. -O.; Linde, C.; Åkermark, B. J. Am. Chem. Soc. 1995, 117, 11035.
14. Related molecules have been incorporated in optically active coronands: a) Hambley, T.W.; Raguse, B.; Ridley, D.D. Aust. J. Chem. 1987, 40, 61. b) Raguse, B.; Ridley, D.D. Ibid. 1986, 39, 1655.
15. Related molecules have been incorporated in optically active coronands: a) Hambley, T.W.; Raguse, B.; Ridley, D.D. Aust. J. Chem. 1987, 40, 61. b) Raguse, B.; Ridley, D.D. Ibid. 1986, 39, 1655.
16. a) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239.
17. b) Johnson, C.R.; Kirchhoff, R.A.; Corkins, H.G. Ibid. 1974, 39, 2458.
18. We recently reported the synthesis of (2-methoxyphenyl)-methylsulfoxime by a reaction sequence involving Kagan's method for sulfide oxidation followed by sequential stereospecific imination with MSH [a) Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625. b) Bolm, C.; Müller, P. Acta Chem. Scand. 1996, 50, 305]. In preliminary studies we showed that this sulfoximine can also be linked by using 5 [c) Bolm, C.; Bienewald, F.; Olvermann, G. unpublished].
19. We recently reported the synthesis of (2-methoxyphenyl)-methylsulfoxime by a reaction sequence involving Kagan's method for sulfide oxidation followed by sequential stereospecific imination with MSH [a) Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625. b) Bolm, C.; Müller, P. Acta Chem. Scand. 1996, 50, 305]. In preliminary studies we showed that this sulfoximine can also be linked by using 5 [c) Bolm, C.; Bienewald, F.; Olvermann, G. unpublished].
20. We recently reported the synthesis of (2-methoxyphenyl)-methylsulfoxime by a reaction sequence involving Kagan's method for sulfide oxidation followed by sequential stereospecific imination with MSH [a) Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625. b) Bolm, C.; Müller, P. Acta Chem. Scand. 1996, 50, 305]. In preliminary studies we showed that this sulfoximine can also be linked by using 5 [c) Bolm, C.; Bienewald, F.; Olvermann, G. unpublished].
21. Johnson, C.R.; Lavergne, O. J. Org. Chem. 1993, 58, 1922.
22. This method has been applied to various substrates (Bolm, C.; Bienewald, F.; Moll, G. to be published).
23. Details of the crystal structure determinations may be obtained from the Director of the Cambridge Crystallographic Data Center, University of Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW (UK) on quoting the full journal citation.
24. Selected bond lengths [Å] and angles [deg] for (S,S)-2c: S(1)-O(1) 1.440(5), S(1)-N(1) 1.517(6), O(1)-S(1)-N(1) 120.9(3), N(1)-S(1)-C(1) 102.1(3), N(1)-S(1)-C(7) 110.6(3), S(1)-N(1)-C(14) 113.2(5).
25. Selected bond lengths [Å] and angles [deg] for (S,S)-9: V(1)-O(3) 1.585(3), V(1)-O(2) 1.938(3), V(1)-O(2′) 1.924(3), V(1)-N(1) 2.055(3), V(1)-N(1′) 2.050(3), S(1)-O(1) 1.442(3), S(1′)-O(1′) 1.441(3), S(1)-N(1) 1.557(3), S(1′)-N(1′) 1.551(3), O(2)-V(1)-N(1) 87.31(12), O(2′)-V(1)-N(1′) 86.96(11), O(3)-V(1)-N(1) 110.1(2), O(3)-V(1)-N(1′) 104.94(14), O(1)-S(1)-N(1) 115.0(2), O(1′)-S(1′)-N(1′) 118.8(2), O(2′)-V(1)-N(1) 140.53(12).
26. For an excellent review on vanadium compounds: Rehder, D. Angew. Chem. 1991, 103, 152; Angew. Chem. Int. Ed. Engl. 1991, 30, 148.
27. For an excellent review on vanadium compounds: Rehder, D. Angew. Chem. 1991, 103, 152; Angew. Chem. Int. Ed. Engl. 1991, 30, 148.
28. max = 42%).
29. Salen/vanadium complexes have been used in this reaction (ref. 6). For a related study: Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640.
30. Salen/vanadium complexes have been used in this reaction (ref. 6). For a related study: Bolm, C.; Bienewald, F. Angew. Chem. 1995, 107, 2883; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640.
31. The low turnover numbers of metal salen catalysts have been attributed to the susceptibility of the imine to oxidative decomposition (Collman, J.P.; Zhang, X.; Lee, V.J.; Uffelman, E.S.; Brauman, J.I. Science 1993, 261, 1404). We expect sulfoximines to be more stable giving catalysts with longer lifetimes.