Stereoselective synthesis of 2-methylenepyrrolizidines by tandem cyclization of N-propargylaminyl radicals

Tetrahedron

Volumn 59, Issue 6, 2003, Pages 827-832

  Hasegawa, Hikaru ^a   Senboku, Hisanori ^a   Kajizuka, Yoshinori ^a   Orito, Kazuhiko ^a   Tokuda, Masao ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Aminyl radical; N chloroamine; Pyrrolizidine; Tandem radical cyclization

Indexed keywords

AMINE; PYRROLIZIDINE DERIVATIVE; RADICAL; TRIBUTYLTIN;

ARTICLE; CHLORINATION; CYCLIZATION; GEOMETRY; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0037415439     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01613-7     Document Type: Article

References (36)

1. Reviews: (a) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237-1286 (b) Bunce R.A. Tetrahedron. 51:1995;13103-13159 (c) Parsons P.J., Penkett C.S., Shell A.J. Chem. Rev. 96:1996;195-206 (d) Malacria M. Chem. Rev. 96:1996;289-306 (e) Dhimane A.-L., Fensterbank L., Malacria M. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Radicals in Organic Synthesis. Vol. 2:2001;350-382 Wiley/VCH, Weinheim.
2. Reviews: (a) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237-1286 (b) Bunce R.A. Tetrahedron. 51:1995;13103-13159 (c) Parsons P.J., Penkett C.S., Shell A.J. Chem. Rev. 96:1996;195-206 (d) Malacria M. Chem. Rev. 96:1996;289-306 (e) Dhimane A.-L., Fensterbank L., Malacria M. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Radicals in Organic Synthesis. Vol. 2:2001;350-382 Wiley/VCH, Weinheim.
3. Reviews: (a) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237-1286 (b) Bunce R.A. Tetrahedron. 51:1995;13103-13159 (c) Parsons P.J., Penkett C.S., Shell A.J. Chem. Rev. 96:1996;195-206 (d) Malacria M. Chem. Rev. 96:1996;289-306 (e) Dhimane A.-L., Fensterbank L., Malacria M. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Radicals in Organic Synthesis. Vol. 2:2001;350-382 Wiley/VCH, Weinheim.
4. Reviews: (a) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237-1286 (b) Bunce R.A. Tetrahedron. 51:1995;13103-13159 (c) Parsons P.J., Penkett C.S., Shell A.J. Chem. Rev. 96:1996;195-206 (d) Malacria M. Chem. Rev. 96:1996;289-306 (e) Dhimane A.-L., Fensterbank L., Malacria M. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Radicals in Organic Synthesis. Vol. 2:2001;350-382 Wiley/VCH, Weinheim.
5. Reviews: (a) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237-1286 (b) Bunce R.A. Tetrahedron. 51:1995;13103-13159 (c) Parsons P.J., Penkett C.S., Shell A.J. Chem. Rev. 96:1996;195-206 (d) Malacria M. Chem. Rev. 96:1996;289-306 (e) Dhimane A.-L., Fensterbank L., Malacria M. Renaud P., Sibi M.P. Radicals in Organic Synthesis. Radicals in Organic Synthesis. Vol. 2:2001;350-382 Wiley/VCH, Weinheim.
6. Recent examples: (a) Zhou S., Bommezijn S., Murphy J.A. Org. Lett. 4:2002;443-445 (b) Njardarson J.T., McDonald I.M., Spiegel D.A., Inoue M., Wood J.L. Org. Lett. 3:2001;2435-2438 (c) Toyota M., Yokota M., Ihara M. J. Am. Chem. Soc. 123:2001;1856-1861 (d) Hilton S.T., Ho T.C.T., Pljevaljcic G., Schulte M., Jones K. Chem. Commun. 2001;209-210.
7. Recent examples: (a) Zhou S., Bommezijn S., Murphy J.A. Org. Lett. 4:2002;443-445 (b) Njardarson J.T., McDonald I.M., Spiegel D.A., Inoue M., Wood J.L. Org. Lett. 3:2001;2435-2438 (c) Toyota M., Yokota M., Ihara M. J. Am. Chem. Soc. 123:2001;1856-1861 (d) Hilton S.T., Ho T.C.T., Pljevaljcic G., Schulte M., Jones K. Chem. Commun. 2001;209-210.
8. Recent examples: (a) Zhou S., Bommezijn S., Murphy J.A. Org. Lett. 4:2002;443-445 (b) Njardarson J.T., McDonald I.M., Spiegel D.A., Inoue M., Wood J.L. Org. Lett. 3:2001;2435-2438 (c) Toyota M., Yokota M., Ihara M. J. Am. Chem. Soc. 123:2001;1856-1861 (d) Hilton S.T., Ho T.C.T., Pljevaljcic G., Schulte M., Jones K. Chem. Commun. 2001;209-210.
9. Recent examples: (a) Zhou S., Bommezijn S., Murphy J.A. Org. Lett. 4:2002;443-445 (b) Njardarson J.T., McDonald I.M., Spiegel D.A., Inoue M., Wood J.L. Org. Lett. 3:2001;2435-2438 (c) Toyota M., Yokota M., Ihara M. J. Am. Chem. Soc. 123:2001;1856-1861 (d) Hilton S.T., Ho T.C.T., Pljevaljcic G., Schulte M., Jones K. Chem. Commun. 2001;209-210.
10. Reviews for pyrrolizidine alkaloids: (a) Robins D.J. Nat. Prod. Rep. 1993;487-496 (b) Liddell R. Nat. Prod. Rep. 1997;653-660.
11. Reviews for pyrrolizidine alkaloids: (a) Robins D.J. Nat. Prod. Rep. 1993;487-496 (b) Liddell R. Nat. Prod. Rep. 1997;653-660.
12. Reviews for indolizidine and quinolizidine alkaloids: (a) Michael J.P. Nat. Prod. Rep. 1995;535-552 (b) Michael J.P. Brossi A. The Alkaloids. Vol. 55:2001;91-267 Academic Press Inc, New York. Chapter 2.
13. Reviews for indolizidine and quinolizidine alkaloids: (a) Michael J.P. Nat. Prod. Rep. 1995;535-552 (b) Michael J.P. Brossi A. The Alkaloids. Vol. 55:2001;91-267 Academic Press Inc, New York. Chapter 2.
14. (a) Bowman W.R., Clark D.N., Marmon R.J. Tetrahedron. 50:1994;1295-1310
15. (b) Bowman W.R., Stephenson P.T., Young A.R. Tetrahedron Lett. 36:1995;5623-5626
16. (c) Smaele D.D., Bogaert P., Kimpe N.D. Tetrahedron Lett. 39:1998;9797-9800
17. (d) Baker S.R., Burton K.I., Parsons A.F., Pons J.-F., Wilson M. J. Chem. Soc., Perkin Trans. 1. 1999;427-436.
18. Reviews for nitrogen radical: (a) Stella L. Angew. Chem., Int. Ed. Engl. 22:1983;337-422 (b) Esker J.L., Newcomb M. Adv. Heterocycl. Chem. 58:1993;1-45 (c) Fallis A.G., Brinza I.M. Tetrahedron. 53:1997;17543-17594 (d) Bowman W.R., Bridge C.F., Brookes P. J. Chem. Soc., Perkin Trans. 1. 2000;1-14.
19. Reviews for nitrogen radical: (a) Stella L. Angew. Chem., Int. Ed. Engl. 22:1983;337-422 (b) Esker J.L., Newcomb M. Adv. Heterocycl. Chem. 58:1993;1-45 (c) Fallis A.G., Brinza I.M. Tetrahedron. 53:1997;17543-17594 (d) Bowman W.R., Bridge C.F., Brookes P. J. Chem. Soc., Perkin Trans. 1. 2000;1-14.
20. Reviews for nitrogen radical: (a) Stella L. Angew. Chem., Int. Ed. Engl. 22:1983;337-422 (b) Esker J.L., Newcomb M. Adv. Heterocycl. Chem. 58:1993;1-45 (c) Fallis A.G., Brinza I.M. Tetrahedron. 53:1997;17543-17594 (d) Bowman W.R., Bridge C.F., Brookes P. J. Chem. Soc., Perkin Trans. 1. 2000;1-14.
21. Reviews for nitrogen radical: (a) Stella L. Angew. Chem., Int. Ed. Engl. 22:1983;337-422 (b) Esker J.L., Newcomb M. Adv. Heterocycl. Chem. 58:1993;1-45 (c) Fallis A.G., Brinza I.M. Tetrahedron. 53:1997;17543-17594 (d) Bowman W.R., Bridge C.F., Brookes P. J. Chem. Soc., Perkin Trans. 1. 2000;1-14.
22. Tokuda M., Fujita H., Suginome H. J. Chem. Soc., Perkin Trans. 1. 1994;777-778.
23. Clark A.J., Deeth R.J., Samuel C.J., Wongtap H. Synlett. 1999;444-446.
24. Newcomb M., Marquardt D.J., Deeb T.M. Tetrahedron. 46:1990;2329-2344.
25. Spellmeyer D.C., Houk K.N. J. Org. Chem. 52:1987;959-974.
26. Senboku H., Hasegawa H., Orito K., Tokuda M. Heterocycles. 50:1999;333-340.
27. Senboku H., Kajizuka Y., Hasegawa H., Fujita H., Suginome H., Orito K., Tokuda M. Tetrahedron. 55:1999;6465-6474.
28. Abdel-Magid A.F., Carson K.G., Harris B.D., Maryanoff C.A., Shah R.D. J. Org. Chem. 61:1996;3849-3862.
29. Moretti I., Torre G. Synthesis. 1970;141.
30. A similar result was shown in Ref. 5a.
31. (a) Beckwith A.L.J. Tetrahedron. 37:1981;3073-3100
32. (b) Beckwith A.L.J., Schiesser C.H. Tetrahedron. 41:1985;3925-3941
33. (c) Broeker J.L., Houk K.N. J. Org. Chem. 56:1991;3651-3655. and also see: Ref. 7d.
34. For ketones 1b, 1c and 1f: Tokuda M., Miyamoto T., Fujita H., Suginome H. Tetrahedron. 47:1991;747-756. and also see Ref. 8. For ketone 2a, see: Ref. 11.
35. Davies L.B., Greenberg S.G., Sammes P.G. J. Chem. Soc., Perkin Trans. 1. 1981;1909-1912.
36. Condon-Gueugnot S., Dupré D., Nédélec J.-Y., Périchon J. Synthesis. 1997;1457-1460.