Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones. Part 1: N-acyliminium ion cyclisations with an internal arene nucleophile

Tetrahedron

Volumn 60, Issue 5, 2004, Pages 1235-1246

  Bahajaj, Abood A ^a   Moore, Madeleine H ^a   Vernon, John M ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Diastereoselective; N Acyliminium ions; Spiro lactams

Indexed keywords

ALUMINUM CHLORIDE; ETHANE; IMINE; INDOLE DERIVATIVE; ION; KETONE DERIVATIVE; LACTAM; NAPHTHALENE DERIVATIVE; PIPERIDINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PYRROLIDINE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; ATOM; CYCLIZATION; ISOMERIZATION; PRIORITY JOURNAL; RACEMIZATION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ARENE;

EID: 0346969559     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.128     Document Type: Article

References (37)

1. Speckamp W.N., Hiemstra H. Tetrahedron. 41:1985;4367-4416.
2. Speckamp W.N., Moolenaar M.J. Tetrahedron. 56:2000;3817-3856. and references therein.
3. Schoemaker H.E., Speckamp W.N. Tetrahedron Lett. 1978;1515-1518.
4. Schoemaker H.E., Speckamp W.N. Tetrahedron. 36:1980;951-958.
5. Evans D.A., Thomas E.W. Tetrahedron Lett. 1979;411-414.
6. Evans D.A., Thomas E.W., Cherpeck R.E. J. Am. Chem. Soc. 104:1982;3695-3700.
7. Inoue Y., Tazawa N., Watanabe A., Aoki Y., Kakisawa H. Bull. Chem. Soc. Jpn. 65:1992;2866-2868.
8. Ito T., Yamazaki N., Kibayashi C. Synlett. 2001;1506-1509.
9. Sun P., Sun C., Weinreb S.M. Org. Lett. 3:2001;3507-3510.
10. Abe H., Aoyagi S., Kibayashi C. Angew. Chem., Int. Ed. 41:2002;3017-3020.
11. Bailey P.D., Morgan K.M., Smith D.I., Vernon J.M. Tetrahedron Lett. 35:1994;7115-7118.
12. Bailey P.D., Morgan K.M., Smith D.I., Vernon J.M. Tetrahedron. 59:2003;3369-3378.
13. Padwa A., Heidelbaugh T.M., Kuethe J.T., McClure M.S. J. Org. Chem. 63:1998;6778-6779.
14. Preliminary publication of some of these results: Bahajaj A.A., Bailey P.D., Moore M.H., Morgan K.M., Vernon J.M. J. Chem. Soc., Chem. Commun. 1994:1994;2511-2512.
15. Romo D., Meyers A.I. Tetrahedron. 47:1991;9503-9569. and references therein.
16. Meyers A.I. Trost B.M. Stereocontrolled organic synthesis. 1994;145-161 Blackwell Scientific, Oxford.
17. Meyers A.I., Brengel G.P. J. Chem. Soc., Chem. Commun. 1997;1-8.
18. Meyers A.I., Burgess L.E. J. Org. Chem. 56:1991;2294-2296.
19. Burgess L.E., Meyers A.I. J. Am. Chem. Soc. 113:1991;9858-9859.
20. Burgess L.E., Meyers A.I. J. Org. Chem. 57:1992;1656-1662.
21. Amat M., Llor N., Bosch J. Tetrahedron Lett. 35:1994;2223-2226.
22. Munchhof M.J., Meyers A.I. J. Org. Chem. 60:1995;7084-7085.
23. Micouin L., Quirion J.-C., Husson H.-P. Tetrahedron Lett. 37:1996;849-852.
24. Amat M., Llor N., Hidalgo J., Hernández A., Bosch J. Tetrahedron: Asymmetry. 7:1996;977-980.
25. Allin S.M., Northfield C.J., Page M.I., Slawin A.M.Z. Tetrahedron Lett. 38:1997;3627-3630.
26. Allin S.M., Northfield C.J., Page M.I., Slawin A.M.Z. J. Chem. Soc., Perkin Trans. 1. 2000;1715-1721.
27. Some other syntheses of spiro lactams via alkylation of the 5-cyano derivative of 7 are unrelated to our present work: cf. (a) Zhu J., Quirion J.-C., Husson H.-P. J. Org. Chem. 58:1993;6451-6456.
28. Ribeiro C.M.R., de Melo S.J., Bonin M., Quirion J.-C., Husson H.-P. Tetrahedron Lett. 35:1994;7227-7230.
29. Bahajaj, A. A.; Vernon, J. M.; Wilson, G. D. Tetrahedron, 2004, 60, 1247-1253.
30. Bahajaj A.A., Hitchings G.J., Moore M.H., Vernon J.M. J. Chem. Soc., Perkin Trans. 1. 1994;1211-1214.
31. Bahajaj A.A., Vernon J.M. J. Chem. Soc., Perkin Trans. 1. 1996;1041-1046.
32. Fains O., Vernon J.M. Tetrahedron Lett. 38:1997;8265-8266.
33. Staudinger H., Schneider H. Ber. 56:1923;699.
34. Meyers A.I., Lefker B.A., Sowin T.J., Westrum L.J. J. Org. Chem. 4243:1989;4246.
35. The (R)-enantiomer 21 has also been reported: Groaning M.D., Meyers A.I. Tetrahedron Lett. 40:1999;4639-4642.
36. Aguilar N., Moyano A., Pericàs M.A., Riera A. Synthesis. 1998;313-316.
37. Crystallographic data for compounds 30a and 35b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 213789 and 213790, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).