Selective azetidine and tetrahydropyridine formation via Pd-catalyzed cyclizations of allene-substituted amines and amino acids

Organic Letters

Volumn 1, Issue 5, 1999, Pages 717-720

  Rutjes, Floris P J T ^a   Tjen, Kim C M F ^a   Wolf, Larissa B ^a   Karstens, Willem F J ^a   Schoemaker, Hans E ^b   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000837947     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990700c     Document Type: Article

References (49)

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17. Reference 1, p 166.
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20. More recently, similar regiochemistry was observed in lanthanide-catalyzed cyclizations of aminoallenes: Arredondo, V. M.; McDonald, F. E.; Marks, T. J. Am. Chem. Soc. 1998, 120, 4871.
21. Wolf, L. B.; Tjen, K. C. M. F.; Rutjes, F. P. J. T.; Hiemstra, H.; Schoemaker, H. E. Tetrahedron Lett. 1998, 39, 5081.
22. Similar three- vs five-membered ring formation of α-amino allenes was reported recently: Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Osawa, E.; Yamaoka, Y.; Fuji, N.; Ibuka, T. J. Org. Chem. 1999, 64, 2992.
23. Meguro, M.; Yamamoto, Y. J. Org. Chem. 1998, 39, 5421.
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26. (b) Hanack, M.; Haeffner, J. Chem. Ber. 1966, 99, 1077.
27. 2-Amino-4,5-hexadienoic acid (homo-allenylglycine) is a naturally occurring amino acid of which several syntheses have been published. Isolation: Chilton, W. S.; Tsou, G.; Kirk, L.; Benedict, R. G. Tetrahedron Lett. 1968, 6283. Racemic synthesis:
28. (b) Cazes, B.; Djahanbini, D.; Goré, J.; Genêt, J.-P.; Gaudin, J.-M. Synthesis 1988, 983.
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30. (d) Black, D. K.; Landor, S. R. J. Chem. Soc. (C) 1968, 283. (S)-Enantiomer:
31. (e) Baldwin, J. E.; Adlington, R. M.; Basak, A. J. Chem. Soc., Chem Commun. 1984, 1284. (5)-Enantiomer (benzyl ester):
32. (f) Dunn, M. J.; Jackson, R. F. W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210.
33. (a) O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663.
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35. Bailey, W. J.; Pfeifer, C. R. J. Org. Chem. 1955, 20, 1337.
36. 2O, pH ∼9), extraction from the water layer, and precipitation upon hydrolysis in acetone using 1 equiv of HCl.
37. The aminopeptidase was generously provided by DSM Research.
38. For related examples, see: (a) Schoemaker, H. E.; Boesten, W. H. J.; Broxterman, Q. B.; Roos, E. C.; Kaptein, B.; van den Tweel, W. J. J.; Kamphuis, J.; Rutjes, F. P. J. T. Chimia 1997, 51, 308-311.
39. (b) 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, 225-233.
40. The ee was determined using chiral HPLC (Crownpak CR(+)) following a known protocol: Miyazawa, T.; Iwanaga, H.; Yamada, T.; Kuwata, S. Chem. Express 1991, 6, 887.
41. Boesten, W. H. J.; Cals, M. J. H. U.S. Patent 4 705 752, 1987; Chem. Abstr. 1987, 105, 170617k.
42. Boesten, W. H. J.; Cals, M. J. H. U.S. Patent 4 705 752, 1987; Chem. Abstr. 1987, 105, 170617k.
43. By using an aminopeptidase produced by a genetically modified Escherichia coli strain both enantiomers were produced in a single run in >98% ee. This experiment, however, has not yet been carried out on a preparative scale. Sonke, T.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis Handbook; Patel, R. N., Ed.; Marcel Dekker, in press.
44. A similar ring expansion (from three- to five-membered rings) has been reported previously: Fugami, K.; Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 857.
45. Review: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
46. -1; F(000) = 488, -25°C. Final R = 0.040 for 1064 observed reflections. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-114107.
47. An alternative cyclization mechanism-activation of the allene by the organopalladium(II) species as the π-complex followed by nucleophilic attack of the nitrogen, which has been proposed by Walkup (ref 3c,d) and Gallagher (ref 2f), cannot be ruled out.
48. For a similar discussion, see: Ahmar, M.; Cazes, B.; Goré, J. Tetrahedron Lett. 1985, 26, 3795.
49. The four- to six-membered ring isomerization was proven in a separate experiment via subjection of 25a to the cyclization conditions, resulting in complete conversion into the tetrahydropyridine 25b.