Ruthenium-catalyzed ring closing olefin metathesis of non-natural α-amino acids

Tetrahedron Letters

Volumn 38, Issue 4, 1997, Pages 677-680

  Rutjes, Floris P J T ^a   Schoemaker, Hans E ^b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALPHA AMINO ACID; AMINO ACID DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031031663     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02390-8     Document Type: Article

References (24)

1. For reviews, see: (a) Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446;
2. (b) Schmalz, H.-G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1833.
3. (a) Nguyen, S.T.; Grubbs, R.H.; Ziller, J.W. J. Am. Chem. Soc. 1993, 115, 9858;
4. (b) Schwab, P.; France, M.B.; Ziller, J.W.; Grubbs, R.H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039.
5. For some recent examples, see: (a) Huwe, C.M.; Kiehl, O.C.; Blechert, S. Synlett 1996, 65;
6. (b) Overkleeft, H.S.; Pandit, U.K. Tetrahedron Lett. 1996, 37, 547;
7. (c) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942;
8. (d) Barrett, A.G.M.; Baugh, S.P.D.; Gibson, V.C.; Giles, M.R.; Marshall, E.L.; Procopiou, P.A. J. Chem. Soc. Chem. Commun. 1996, 2231.
9. (a) Clark, T.D.; Ghadiri, M.R. J. Am. Chem. Soc. 1995, 117, 12364;
10. (b) Miller, S.J.; Blackwell, H.E.; Grubbs, R.H. J. Am. Chem. Soc. 1996, 118, 9606
11. (c) Garro-Hélion, F.; Guibé, F. J. Chem. Soc. Chem. Commun. 1996, 641.
12. (a) Schuster, M.; Pernerstorfer, J.; Blechert, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1979;
13. (b) Maarseveen, J.H.; Den Hartog, J.A.J.; Engelen, V.; Visser, G.; Kruse, C.G. Tetrahedron Lett. 1996, 37, 8249.
14. For an entry into this area, see: Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244.
15. For a recent review, see e.g.: Schoemaker, H.E.; Boesten, W.H.J.; Kaptein, B.; Roos, E.C.; Broxterman, Q.B.; van den Tweel, W.J.J.; Kamphuis, J. Acta Chem. Scand. 1996, 50, 225.
16. Both D- and L-allylglycine are commercially available, but can also be obtained in enantiopure form through enzymatic resolution, see: Broxterman, Q.B.; Kaptein, B.; Kamphuis, J.; Schoemaker, H.E. J. Org. Chem. 1992, 57, 6286.
17. Obtained via resolution with an amidase from Mycobacterium neoaurum, see: Kaptein, B.; Boesten, W.H.J.; Broxterman, Q.B.; Peters, P.J.H.; Schoemaker, H.E.; Kamphuis, J. Tetrahedron: Asymmetry 1993, 4, 1113.
18. 13C NMR spectroscopy, high resolution mass data and rotation values.
19. 2).
20. Analysis on a Chiralpak AS column (10% i-PrOH in heptane) showed an ee of >99%.
21. 3 (M+H) 276.1600, found 276.1595.
22. (a) O'Donnell, M.J.; Polt, R.L. J. Org. Chem. 1982, 47, 2663;
23. (b) O'Donnell, M.J.; Wojciechowski, K. Synthesis 1984, 313.
24. Miyazawa, T.; Iwanaga, H.; Yamada, T.; Kuwata, S. Chem. Express 1991, 6, 887.