The Lewis acid catalysed addition of 1-trimethylsilyl nitropropanate to imines

Synlett

Volumn , Issue 6, 2000, Pages 850-852

  Anderson, James C ^a   Peace, Simon ^a   Pih, Steven ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Amines; Catalysis; Diastereoselectivity; Imines; Samarium

Indexed keywords

AMMONIUM NITRATE; IMINE; SAMARIUM; TRIFLUOROMETHANESULFONIC ACID; UREA DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034122358     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Adams, H; Anderson, J.C.; Peace, S.; Pennell, A.M.K. J. Org. Chim. 1998, 63, 9932.
2. Sturgess, M.A.; Yarberry, D.J. Tetrahedron Lett. 1993, 34, 4743.
3. Kende, A.S.; Mendoza, J.S. Tetrahedron Lett. 1991, 32, 1699.
4. Smith, A.B., III; Leahy, J.W.; Noda, I.; Remiszewski, S.W.; Liverton, N.J.; Zibuck, R. J. Am. Chem. Soc. 1992, 114, 2995.
5. (a) Kise, N.; Kashiwagi, K.; Watanabe, M.; Yoshida, J. J. Org. Chem. 1996, 61, 428.
6. (b) Park, Y.S.; Boys, M.L.; Beak, P. J. Am. Chem. Soc. 1996, 118, 3757.
7. Nielsen, A.T. In The Chemistry of the Nitro and Nitroso Group, Part I; Patai, S. Ed.; Wiley Interscience: New York, 1969; pp 349.
8. a, (propane-nitronic acid) = 4.6 (in water, ref. 6)
9. a (N-benzylidenebenzylamine) ∼7 (see: (a) Koehler, K.; Sandstron, W.; Cordes, E.H. J. Am. Chem. Soc. 1964, 86, 2413.
10. (b) Cordes, E.H.; Jencks, W.P. J. Am. Chem. Soc. 1963, 85, 2843.)
11. Peace, S. PhD Thesis, University of Sheffield, 1996.
12. Catalytic Enantioselective Addition to Imines, Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
13. Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153.
14. Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474.
15. For example see (a) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
16. (b) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1997, 119, 10049.
17. (c) Loh, T.-P.; Wei, L.-L. Tetrahedron Lett. 1998, 39, 323.
18. (d) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
19. Kobayashi, S.; Akiyama, R.; Kawamura, M.; Ishitani, H. Chem. Lett. 1997, 1039.
20. For reviews see(a) Kobayashi, S. Eur. J. Org. Chem. 1999, 15.
21. (b) Cotton, S.A. Cotton Polyhedron 1999, 18, 1691.
22. For the synthesis of trimethylsilyl nitronates see (a) Kashutina, M.V.; Joffe, S.L.; Joffe, V.A. Doklady Akad. Nauk. S.S.S.R. 1974, 218, 109.
23. (b) Torssell, K.; Zenthen, O. Acta Chem. Scand. 1978, B32, 11.
24. nBuLi (30mL of a 2.4 M solution in hexanes, 66mmol) at -78 °C. The resulting mixture was vigorously stirred until the yellow colour had dispersed (∼40min), whereupon TMSCl (9.1mL, 72mmol) in THF (30mL+2 × 5mL wash) was added. The reaction was removed from the cold bath and allowed to r.t. Removal of the solvent in vacuo at sub ambient temperature afforded a yellow slurry which was treated with light petroleum ether (250mL), filtered and evaporated to dryness at sub ambient temperature. The residue was gently distilled under high vacuum (∼0.05 mmHg) with the warmth of the hand and the receiver flask cooled to -78 °C to give l-trimethylsilyl nitropropanate (3.8g, 40%).
25. 6 major δ 4.51 (J = 6.3), minor δ 4.39 (J = 8.6). A similar analysis was used for the other assignments.
26. 2= PMP) by single X-ray cyrstallography. Pih, S. PhD Thesis, University of Nottingham, in preparation.
27. Kronenthal, D.R.; Han, C.Y.; Taylor, M.K. J. Org. Chem. 1982, 47, 2765.
28. 2O calcd. 190.1107, found 190.1106.