Nucleophile-dependent stereodivergence in the Pd-catalyzed intramolecular cyclization of 2-(p-tolylsulfinyl)allylacetates

Tetrahedron Letters

Volumn 40, Issue 22, 1999, Pages 4259-4262

  Henrich, Marielouise ^a   Delgado, Antonio ^b   Molins, Elies ^c   Roig, Anna ^c   Llebaria, Amadeu ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM COMPLEX; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; MOLECULAR INTERACTION; STEREOISOMERISM; STRUCTURE ANALYSIS; X RAY ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0033612263     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00701-7     Document Type: Article

References (22)

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2. b) Tsuji, J. Palladium Reagents and Catalysts, Wiley, Chichester, 1995;
3. c) Takacs, J.M. in Comprehensive Organometallic Chemistry II, Vol.12 (Eds.: Abel, E.W.; Stone, F.G.A.; Wilkinson, G.; Hegedus, L.S.), Pergamon, Oxford, 1995, pp.785-904.
4. a) Trost, B.M. Angew. Chem. Int. Ed. Eng. 1989, 101, 1173-1192;
5. b) Heumann, A.; Réglier, A. Tetrahedron 1995, 51, 975-1015.
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7. b) Trost, B.M. Acc. Chem. Res. 1996, 29, 355-364.
8. Metz, P. Methoden Org. Chem. (Houben-weyl), Vol.E21, pp. 5643-5668.
9. Primary or secondary amines, or anionic nucleophiles such as azides and imide or sulfonamide salts are the usual nucleophiles, whereas the corresponding carbamate or carboxamide salts are recognized to be poor nucleophiles in reactions with π-allyl palladium intermediates. See, for example: a) Inoue, Y.; Taguchi, M.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1985, 58, 2721-2722;
10. b) Takagi, M.; Yamamoto, K. Chem. Lett. 1989, 2123-2124; see also ref. 7a.
11. Johannsen, M.; Jorgensen, K.A. Chem. Rev. 1998, 98, 1689-1708.
12. For Pd(0) catalyzed intramolecular carbamate cyclizations involving π-allyl-palladium intermediates, see: K. Takano, K.; Nigawara, Y.; Nishino, E.; Takagi, I.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681-5704.
13. For Pd(II) catalyzed intramolecular cyclizations not involving π-allyl-palladium intermediates, see: a) Hirai, Y.; Watanabe, J.; Nozaki, T.; Yokoyama, H.; Yamaguchi, S. J. Org. Chem. 1997, 62, 776-777;
14. b) Yokoyama, H.; Otaya, K.; Yamaguchi, S.; Hirai, Y. Tetrahedron Lett. 1998, 39, 5971-5974.
15. Trost, B.M.; Van Vranken, D.L. J. Am. Chem. Soc. 1993, 115, 444-458.
16. Carreño, M.C. Chem. Rev. 1995, 95, 1717-1760.
17. Reactions of sulfinyl-substituted π-allyl palladium complexes: a) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153-156;
18. b) Hiroi, K.; Onuma, H.; Arinaga, Y. Chem. Lett. 1995, 1099-2000.
19. At short reaction times or when NaH was absent, formation of the primary acetate resulting from 1,3-allylic rearrangement of the acetoxy group was observed. See: a) Trost, B.M.; Verhoeven, T.R.; Fortunak, J.P. Tetrahedron Lett. 1979, 2301-2304
20. b) Trost, B.M.; Organ, M.G. J. Am Chem. Soc. 1994, 116, 10320-10321.
21. We could temptatively assign the stereochemistry of the major piperidines as being the same as the major pyrrolidines in N-Boc and trifluoracetamide series, based on the assumption that a similar mechanism operated for 5 and 6 membered cyclizations. No suitable crystals for X-ray analysis could be obtained in the piperidine series. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as a supplementary publication n° CCDC-102450. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
22. Reductive elimination in palladium-catalyzed aryl amination: Mann, G.; Hartwig, J.F.; Driver, M.S.; Fernández-Rivas, C. J. Am Chem. Soc. 1998, 120, 827-828 and references therein. For a related aryl amidation, see: Wolfe, J.P.; Rennels, R.A.; Buchwald, S.L. Tetrahedron 1996, 52, 7525-7546.