Catalytic enantioselective Michael addition reactions of α-nitroesters to α,β-unsaturated ketones

Tetrahedron Asymmetry

Volumn 8, Issue 20, 1997, Pages 3403-3413

  Keller, Erik ^a   Veldman, Nora ^b   Spek, Anthony L ^b   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; KETONE; NITRO DERIVATIVE; ORGANIC COMPOUND;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STOICHIOMETRY; TEMPERATURE DEPENDENCE;

EID: 0030669550     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00432-1     Document Type: Article

References (35)

1. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series, No. 9, Pergamon: Oxford 1992.
2. Feringa, B. L.; de Vries, A. H. M. Carbon-Carbon Bond Formation by Catalytic Enantioselective Conjugate Addition; in Advances in Catalytic Processes; JAI Press Inc.; Vol. 1, 151-192, 1995.
3. Smalz, H.-G. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds.; Pergamon: Oxford 1991.
4. For a very efficient Michael addition (MA) of dialkylmalonates, see: Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571; Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 111, 6194.
5. For a very efficient Michael addition (MA) of dialkylmalonates, see: Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571; Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 111, 6194.
6. For a recent example of an enantioselective MA of β-ketoesters, see: Sasai, H., Emori, E., Arai, T., Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561.
7. Wijnberg, H.; Helder, R. Tetrahedron Lett. 1975, 46, 4057.
8. Coda, A. C.; Desimoni, G.; Invernizzi, A. G.; Righetti, P. P.; Seneci, P. F.; Tacconi, G. Gazz. Chim. It. 1985, 115, 111.
9. de Vries, A. H. M.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374; de Vries, A. H. M.; Feringa, B. L. Tetrahedron 1994, 50, 4479.
10. de Vries, A. H. M.; Feringa, B. L. Angew. Chem. Int. Ed. Engl. 1996, 35, 2374; de Vries, A. H. M.; Feringa, B. L. Tetrahedron 1994, 50, 4479.
11. Keller, E.; Feringa, B. L. Tetrahedron 1996, 37, 1879.
12. Keller, E.; Feringa, B. L. Synlett 1997, 842.
13. Steinhagen, H.; Helmchen, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 2339.
14. Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418; Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851; Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 855; Sasai, H.; Suzuki, T.; Itoh, N.; Arai, S.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 2657; Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Tadamasa, D.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372.
15. Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418; Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851; Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 855; Sasai, H.; Suzuki, T.; Itoh, N.; Arai, S.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 2657; Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Tadamasa, D.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372.
16. Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418; Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851; Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 855; Sasai, H.; Suzuki, T.; Itoh, N.; Arai, S.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 2657; Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Tadamasa, D.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372.
17. Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418; Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851; Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 855; Sasai, H.; Suzuki, T.; Itoh, N.; Arai, S.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 2657; Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Tadamasa, D.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372.
18. Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418; Sasai, H.; Suzuki, T.; Itoh, N.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 851; Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 855; Sasai, H.; Suzuki, T.; Itoh, N.; Arai, S.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 2657; Sasai, H.; Suzuki, T.; Itoh, N.; Tanaka, K.; Tadamasa, D.; Okamura, K.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 10372.
19. The optical purity of 4a was determined by HPLC analysis on chiral stationary phase (DAICEL CHIRALPAK OJ), after conversion to the corresponding 1,3-dioxolane.
20. Arai, T.; Sasai, H.; Aoe, K.-i.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 104; Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926.
21. Arai, T.; Sasai, H.; Aoe, K.-i.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 104; Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926.
22. The absolute configuration of the major enantiomer has not been established so far.
23. 14 This is probably not an accurate figure since 'AlLiBINOL' appears to be a mixture of aluminium complexes in solution.
24. The e.e. of Michael adduct 4b could be determined directly by HPLC analysis on a chiral stationary phase (DAICEL CHIRALPAK AD).
25. Starting material is recovered, even after prolonged reaction time.
26. Polymerisation of the Michael acceptor is observed.
27. 13C NMR (125 MHz).
28. Also three THF molecules were present in the crystal structure.
29. Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368.
30. Benn, R.; Janssen, E.; Lehmkuhl, H.; Rufinska, A. J. Organomet. Chem. 1987, 333, 181; Delpuech, J. J.; Khaddar, M. R.; Peguy, A. A.; Rubini, P. R. J. Am. Chem. Soc. 1975, 97, 3373.
31. Benn, R.; Janssen, E.; Lehmkuhl, H.; Rufinska, A. J. Organomet. Chem. 1987, 333, 181; Delpuech, J. J.; Khaddar, M. R.; Peguy, A. A.; Rubini, P. R. J. Am. Chem. Soc. 1975, 97, 3373.
32. Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225.
33. Kornblum, N.; Blackwood, R. K. Organic Synthesis; John Wiley & Sons, New York, 1963, Collect. Vol. 4, 454.
34. Lau, H.-H; Schollkopf, U. Liebigs Ann. Chem. 1981, 1378.
35. Mixture for TLC staining: o-anisaldehyde dip: (mix at 0°C) anisaldehyde 7.4 mL; ethanol (96%) 383 mL; sulfuric acid 10 mL; acetic acid 3.0 mL.