Synthesis of 2-substituted nitrogen heterocycles using para-toluenesulfonyl iodide in a key step

Synlett

Volumn , Issue 12, 1997, Pages 1441-1443

  Craig, D C ^a   Edwards, G L ^a   Muldoon, C A ^a  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013470608     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1057     Document Type: Article

References (28)

1. Pyne, S.G. J. Chem. Soc., Chem. Commun. 1986, 1686.
2. Pyne, S.G.; Chapman, S.L. J. Chem. Soc., Chem. Commun. 1986, 1688.
3. Johnson, S.J. J. Org. Chem. 1995, 60, 8089.
4. Oishi, T.; Iwakuma, T.; Hirama, M.; Itô, S. Synlett 1995, 404.
5. Carretero, J.C.; Arrayds, R.G.; de Gracia, I.S. Tetrahedron Lett. 1996, 37, 3379.
6. Carretero, J.C.; Arrayás, R.G. J. Org. Chem. 1995, 60, 6000.
7. Toyooka, N.; Yotsui, Y.; Yoshida, Y.; Momose, T. J. Org. Chem. 1996, 61, 4882.
8. Edwards, G.L.; Walker, K.A. Tetrahedron Lett. 1992, 33, 1779.
9. Craig, D.C.; Durie, A.; Edwards, G.L.; Sinclair, D.J. Tetrahedron Lett. 1995, 36, 1307.
10. Craig, D.C.; Edwards, G.L.; Muldoon, C.A. Synlett 1997, accepted for publication.
11. Reaction of alkene (1) with tosyl iodide gave complex mixtures (Scheme 6). Addition of one equivalent of tosyl iodide, and then treatment of the crude product with DBU, gave the acyclic sulfonamide (2, 20%), an iodocyclisation product (25, 9%) and the α-(toluenesulfonylmethyl) pyrrolidine (8, 4%). (Chemical Equation Presented)
12. Craig, D.C.; Edwards, G.L.; Muldoon, C.A. Tetrahedron 1997, 53, 6171. The conditions for radical addition of tosyl iodide to alkenols were applied to the protected aminoalkenes.
13. 7
14. Flukabrand™ ChiraSelect Reagent (≥ 99% e.e.) is available from the Aldrich Chemical Company: (R)-enantiomer, 25 ml £67.60; (S)-enantiomer, 25 ml £99.60.
15. Karoyan, P.; Chassaing, G. Tetrahedron Lett. 1997, 38, 85.
16. Lorthiois, E.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 89.
17. Davies, S.G.; Smyth, G.D. Tetrahedron: Asymmetry 1996, 7, 1001.
18. Davies, S.G.; Smyth, G.D. Tetrahedron: Asymmetry 1996, 7, 1273.
19. Fox, D.N.A.; Lathbury, D.; Mahon, M.F.; Molloy, K.C.; Gallagher, T. J. Am. Chem. Soc. 1991, 113, 2652.
20. Juaristi, E.; Murer, P.; Seebach, D. Synthesis 1993, 1243.
21. The crude products contained two mole equivalents of TFA, but could be used without further purification.
22. +, <1 %), 328 (9), 266 (10), 174 (45), 105 (100), 91 (41).
23. 1H NMR), and was not isolated. Cyclisation at room temperature gave a lower yield (47%) of the piperidine and relatively more allyl sulfone (≃40%).
24. Full details of the structures (20) and (22) have been deposited with the Cambridge Crystallographic Data Centre.
25. Fox, D.N.A.; Gallagher, T. Tetrahedron, 1990, 46, 4697.
26. 3
27. Estermann, H.; Seebach, D. Helv. Chim. Acta. 1988, 71, 1824.
28. Rylander, P.N. In Hydrogenation Methods; Academic Press: London, 1985; pp. 163-165.