Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates

Synthesis

Volumn , Issue 14, 2004, Pages 2303-2316

  Özlügedik, Mustafa ^a   Kristensen, Jesper ^b   Reuber, Jenny ^a   Fröhlich, Roland ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

( ) sparteine; 1 alkenyl carbamates; Asymmetric synthesis; Bicyclic lactones; Homoaldol addition

Indexed keywords

ADDITION REACTIONS; ETHERS; LITHIUM COMPOUNDS; NITROGEN COMPOUNDS; OXIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DIASTEREOMERS; STEREOSELECTIVE ADDITION; STEREOSELECTIVE SYNTHESIS;

ALDEHYDES;

ALDEHYDE; BETA NAPHTHYLMETHYL BROMIDE; BICYCLO COMPOUND; CARBAMIC ACID DERIVATIVE; GAMMA LACTONE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM HEXAMETHYLDISILAZIDE; N,N DIISOPROPYLCARBAMATE DERIVATIVE; NAPHTHYL GROUP; SPARTEINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALDOL REACTION; ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 5644250666     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831170     Document Type: Article

References (34)

1. Responsible for X-Ray crystal structure data.
2. Reviews: (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282; Angew. Chem. 1997, 109, 2376.
3. Reviews: (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282; Angew. Chem. 1997, 109, 2376.
4. (b) Hoppe, D.; Marr, F.; Brüggemann, M. In Organolithium in Enantioselective Synthesis, Topics in Organometallic Chemistry, Vol. 5; Hodgson, D. M., Ed.; Springer-Verlag: Berlin, 2003, 61.
5. (c) Beak, P.; Johnson, T. A.; Kim, D. D. In Organolithium in Enantioselective Synthesis, Topics in Organometallic Chemistry, Vol. 5; Hodgson, D. M., Ed.; Springer-Verlag: Berlin, 2003, 134.
6. (d) Ahlbrecht, H.; Beyer, U. Synthesis 1999, 365.
7. (a) Hoppe, D.; Zschage, O. Angew. Chem., Int. Ed. Engl. 1989, 28, 69; Angew. Chem. 1989, 101, 67.
8. (a) Hoppe, D.; Zschage, O. Angew. Chem., Int. Ed. Engl. 1989, 28, 69; Angew. Chem. 1989, 101, 67.
9. (b) Whisler, M. C.; Vaillancourt, L. V.; Beak, P. Org. Lett. 2000, 2, 2655.
10. (c) Seppi, M.; Kalkofen, R.; Reupohl, J.; Fröhlich, R.; Hoppe, D. Angew. Chem. Int. Ed. 2004, 43, 1423; Angew. Chem. 2004, 116, 1147.
11. (c) Seppi, M.; Kalkofen, R.; Reupohl, J.; Fröhlich, R.; Hoppe, D. Angew. Chem. Int. Ed. 2004, 43, 1423; Angew. Chem. 2004, 116, 1147.
12. (d) Reuber, J.; Fröhlich, R.; Hoppe, D. Org. Lett. 2004, 6, 783.
13. Özlügedik, M.; Kristensen, J.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Eur. J. Org. Chem. 2002, 414.
14. Reviews on titanation: (a) Reetz, M. T. Organotitanium Reagents in Organic Synthesis, 1st ed.; Springer-Verlag: Berlin, 1986.
15. (b) Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 32; Angew. Chem. 1983, 95, 12.
16. (b) Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 32; Angew. Chem. 1983, 95, 12.
17. (c) Reetz, M. T. In Organotitanium Chemistry, Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 2002, 817.
18. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
19. 3 as exchange reagent is recommended.3d
20. Hoppe, D.; Hanko, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 372; Angew. Chem. 1982, 94, 378.
21. Hoppe, D.; Hanko, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 372; Angew. Chem. 1982, 94, 378.
22. (a) Hoppe, D.; Brönneke, A. Tetrahedron Lett. 1983, 24, 1687.
23. (b) Hanko, R.; Rabe, K.; Dally, R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1690; Angew. Chem. 1991, 103, 1725.
24. (b) Hanko, R.; Rabe, K.; Dally, R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1690; Angew. Chem. 1991, 103, 1725.
25. Grieco, P. A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett. 1978, 419.
26. Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667.
27. Data sets were collected with an Enraf-Nonius CAD4 diffractometer. Programs used: data collection EXPRESS (Nonius B.V., 1994), data reduction MolEN (K. Fair, Enraf-Nonius B.V., 1990), structure solution SHELXS-97 (Sheldrick, G. M. Acta Cryst. 1990, A46, 467), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics MOPICT 3.2 (M. Brüggemann, Universität Münster, 2001). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 182787 and 182786. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, CambridgeCB2 1EZ, UK [fax: int. code +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].
28. Data sets were collected with an Enraf-Nonius CAD4 diffractometer. Programs used: data collection EXPRESS (Nonius B.V., 1994), data reduction MolEN (K. Fair, Enraf-Nonius B.V., 1990), structure solution SHELXS-97 (Sheldrick, G. M. Acta Cryst. 1990, A46, 467), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics MOPICT 3.2 (M. Brüggemann, Universität Münster, 2001). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 182787 and 182786. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, CambridgeCB2 1EZ, UK [fax: int. code +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].
29. Data sets were collected with an Enraf-Nonius CAD4 diffractometer. Programs used: data collection EXPRESS (Nonius B.V., 1994), data reduction MolEN (K. Fair, Enraf-Nonius B.V., 1990), structure solution SHELXS-97 (Sheldrick, G. M. Acta Cryst. 1990, A46, 467), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics MOPICT 3.2 (M. Brüggemann, Universität Münster, 2001). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 182787 and 182786. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, CambridgeCB2 1EZ, UK [fax: int. code +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].
30. Data sets were collected with an Enraf-Nonius CAD4 diffractometer. Programs used: data collection EXPRESS (Nonius B.V., 1994), data reduction MolEN (K. Fair, Enraf-Nonius B.V., 1990), structure solution SHELXS-97 (Sheldrick, G. M. Acta Cryst. 1990, A46, 467), structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göttingen, 1997), graphics MOPICT 3.2 (M. Brüggemann, Universität Münster, 2001). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 182787 and 182786. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, CambridgeCB2 1EZ, UK [fax: int. code +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].
31. Reviews: (a) Evans, D. A. Stereoselective Alkylation of Chiral Metal Enolates: Asymmetric Synthesis, Vol. 3; Morrison, J. D., Ed.; Academic Press: Orlando, 1984, 1-110.
32. (b) Fráter, G. Alkylation of Ester Enolates In Stereoselective Synthesis (Houben-Weyl), Vol. E21a; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995, 723-790.
33. Prasad, K. R.; Özlügedik, M.; Wibbeling, B.; Fröhlich, R.; Hoppe, D., manuscript in preparation.
34. Determined via the lactone derivative.