Asymmetric lithiation of an allyl carbamate induced by a complexing remote chiral substituent

Synlett

Volumn , Issue 7, 2000, Pages 950-954

  Heimbach, Dirk K ^a   Fröhlich, Roland ^a   Wibbeling, Birgit ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Chiral allyllithium compounds; Chiral N sulfonyl 1,3 oxazolidines; Lithiodestannylation; Stannylation; Stereochemistry of the electrophilic substitution

Indexed keywords

ALLYL COMPOUND; CARBAMIC ACID DERIVATIVE;

ARTICLE; CHELATION; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; THERMODYNAMICS;

EID: 0342647486     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

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2. b) D. Hoppe, Angew. Chem. Int. Ed. Engl. 1984, 23, 239.
3. c) For a related approach see: Weisenburger, G. A.; Faibish, N. C.; Pippel, D. J.; Beak P J. Am. Chem. Soc. 1999, 121, 9522.
4. For some applications in natural product synthesis see: Berque, I.; Le Ménez, P.; Razon, P.; Mahuteau, J.; Férézou, J.-P.; Pancrazi, A.; Ardisson, J.; Brion, J.-D. J. Org. Chem. 1999, 64, 373-381, and references cited therein. Smith, N.D.; Kocienski, P.J.; Street, S.D.A. Synthesis 1996, 652.
5. For some applications in natural product synthesis see: Berque, I.; Le Ménez, P.; Razon, P.; Mahuteau, J.; Férézou, J.-P.; Pancrazi, A.; Ardisson, J.; Brion, J.-D. J. Org. Chem. 1999, 64, 373-381, and references cited therein. Smith, N.D.; Kocienski, P.J.; Street, S.D.A. Synthesis 1996, 652.
6. a) Hoppe, D.; Krämer, T. Angew. Chem Int. Ed. Engl. 1986, 25, 160.
7. a) Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem. Im. Ed. Engl. 1990, 29, 296.
8. b) Hoppe, D.; Krämer, T.; Schwark, J.-R.; Zschage, O Pure Appl. Chem. 1990, 62, 1999.
9. c) Zschage, O.; Schwark, J.-R.; Krämer, T.; Hoppe, D. Tetrahedron 1992, 48, 8377.
10. a) Hoppe, D.; Zschage, O. Angew. Chem. Int. Ed. Engl. 1989, 28, 69.
11. b) Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667.
12. c) Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis 1996, 141.
13. a) Behrens, K.; Fröhlich, R.; Meyer, O.; Hoppe, D. Eur. J. Org. Chem. 1998, 2397.
14. b) Deiters, A.; Hoppe D. Angew. Chem. Int. Ed. 1999, 38, 546.
15. We already have applied a similar strategy to the kinetically controlled diasteroselectivc generation of (configurationally stable) 2-or 3-heterosubstituted 2-lithioalkyl carbamates from chiral precursors. a) Ahrens, H.; Paetow, M.; Hoppe, D.; Tetrahedron Lett. 1992, 33, 5327.
16. b) Helmke, H.; Hoppe, D. Synlett 1995, 978.
17. c) Sendzik, M.; Guarnieri, W.; Hoppe, D. Synthesis 1998, 1287, and cited previous work.
18. Hoppe, I.; Hoffmann, H.; Gärtner, I.; Krettek, T.; Hoppe, D. Synthesis 1991, 1157.
19. 10
20. T. Krettek, Dissertation, Universität Kiel 1993.
21. Hudrlik, P.F.; Peterson, D. J. Am. Chem Soc. 1975, 97, 1464.
22. Winterfeldt, E. Synthesis 1975, 617.
23. Hoppe, D.; Hanko, R.; Brönneke, A.; Lichtenberg, F.; van Hülsen, E. Chem. Ber. 1985, 118, 2822.
24. Data for selected compounds.
25. See ref. [1b] and Tomooka, K.; Shimizu, H.; Inoue, T. Shibata, H.; Nakai, T. Chem. Lett. 1999, 759.
26. -3, Flack parameter 0.01(4), anisotropic thermal parameters indicate severe disorder in the ethyl group (C41, C42) and one of the iso-propyl groups (C361-C363), refinement with split positions did not improve the quality of the analysis, hydrogens calculated and riding. Data sets were collected with Nonius CAD4 and KappaCCD diffractometers, the later one equipped with a rotating anode generator Nonius FR591. Programs used: data collection EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B. V., 1998), data reduction MoIEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326), absorption correction for CCD data SORTAV (R.H. Blessing, Acta Cryst. 1995, A51, 33-37; R.H. Blessing, J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (G.M. Sheldrick, Acta Cryst. 1990, A46, 467-473), structure refinement SHELXL-97 (G.M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, Universität Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CSD-141951 (9b) and CSD-141950 (9d). Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code+44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk].
27. -3, Flack parameter 0.01(4), anisotropic thermal parameters indicate severe disorder in the ethyl group (C41, C42) and one of the iso-propyl groups (C361-C363), refinement with split positions did not improve the quality of the analysis, hydrogens calculated and riding. Data sets were collected with Nonius CAD4 and KappaCCD diffractometers, the later one equipped with a rotating anode generator Nonius FR591. Programs used: data collection EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B. V., 1998), data reduction MoIEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326), absorption correction for CCD data SORTAV (R.H. Blessing, Acta Cryst. 1995, A51, 33-37; R.H. Blessing, J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (G.M. Sheldrick, Acta Cryst. 1990, A46, 467-473), structure refinement SHELXL-97 (G.M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, Universität Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CSD-141951 (9b) and CSD-141950 (9d). Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code+44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk].
28. -3, Flack parameter 0.01(4), anisotropic thermal parameters indicate severe disorder in the ethyl group (C41, C42) and one of the iso-propyl groups (C361-C363), refinement with split positions did not improve the quality of the analysis, hydrogens calculated and riding. Data sets were collected with Nonius CAD4 and KappaCCD diffractometers, the later one equipped with a rotating anode generator Nonius FR591. Programs used: data collection EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B. V., 1998), data reduction MoIEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326), absorption correction for CCD data SORTAV (R.H. Blessing, Acta Cryst. 1995, A51, 33-37; R.H. Blessing, J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (G.M. Sheldrick, Acta Cryst. 1990, A46, 467-473), structure refinement SHELXL-97 (G.M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, Universität Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CSD-141951 (9b) and CSD-141950 (9d). Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code+44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk].
29. -3, Flack parameter 0.01(4), anisotropic thermal parameters indicate severe disorder in the ethyl group (C41, C42) and one of the iso-propyl groups (C361-C363), refinement with split positions did not improve the quality of the analysis, hydrogens calculated and riding. Data sets were collected with Nonius CAD4 and KappaCCD diffractometers, the later one equipped with a rotating anode generator Nonius FR591. Programs used: data collection EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B. V., 1998), data reduction MoIEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology 1997, 276, 307-326), absorption correction for CCD data SORTAV (R.H. Blessing, Acta Cryst. 1995, A51, 33-37; R.H. Blessing, J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (G.M. Sheldrick, Acta Cryst. 1990, A46, 467-473), structure refinement SHELXL-97 (G.M. Sheldrick, Universität Göttingen, 1997), graphics SCHAKAL (E. Keller, Universität Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CSD-141951 (9b) and CSD-141950 (9d). Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code+44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk].
30. The strong influence of the ligand at the lithium cation (see entries 3 and 11 in Table 1) on the regioselectivity of the stannylation reaction is surprising: In the presence of (-)-sparteine, complete γ-selectivity is observed.
31. 4c
32. a) Carstens, A.; Hoppe, D. Tetrahedron 1994, 50, 6097.
33. b) see also Hammerschmidt, F; Hanninger, A.; Peric Simov, B.; Völlenkle, H.; Werner, A. Eur. J. Org. Chem. 1999, 3511.
34. c) Weisenburger, G. A., Faibish, N. C, Pippel, D. J., Beak, P. J. Am. Chem. Soc. 1999, 121, 9522, and references cited therein.
35. Although pathway A may also contribute, it is unimportant for the stereochemical outcome.
36. C. Mück-Lichtenfeld, unpublished results.