Enantioselective synthesis of bicyclic tetrahydrofuran carboxaldehydes from chiral 3-stannylbut-1-enyl carbamates by tandem homoaldol/aldol reaction

Synthesis

Volumn , Issue 1, 1996, Pages 145-148

  Paulsen, Holger ^a   Graeve, Claudia ^a   Fröhlich, Roland ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

8 oxabicyclo 3.2.1 octane 6 carboxaldehydes; chiral allylstannanes; enantioselective homoaldol reaction; intramolecular Mukaiyama aldolization of 8 oxo 1 alkenyl carbamates

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030030150     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4173     Document Type: Article

References (15)

1. Hoppe, D.; Krämer, T.; Freire Erdbrügger, C.; Egert, E. Tetrahedron Lett. 1989, 30, 1233.
2. For related tetrahydrofuran syntheses see: Hoffmann, R. W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem. 1993, 629. Mulzer, J.; Greifenberg, S.; Buschmann, J.; Luger, P. Angew. Chem. 1993, 105, 1214; Angew. Chem., Int. Ed. Engl. 1993, 32, 1173.
3. For related tetrahydrofuran syntheses see: Hoffmann, R. W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem. 1993, 629. Mulzer, J.; Greifenberg, S.; Buschmann, J.; Luger, P. Angew. Chem. 1993, 105, 1214; Angew. Chem., Int. Ed. Engl. 1993, 32, 1173.
4. For related tetrahydrofuran syntheses see: Hoffmann, R. W.; Giesen, V.; Fuest, M. Liebigs Ann. Chem. 1993, 629. Mulzer, J.; Greifenberg, S.; Buschmann, J.; Luger, P. Angew. Chem. 1993, 105, 1214; Angew. Chem., Int. Ed. Engl. 1993, 32, 1173.
5. Reviews for tetrahydrofuran synthesis: Boivin, T. L. Tetrahedron 1987, 43, 3309. Koert, U. Synthesis 1995, 115.
6. Reviews for tetrahydrofuran synthesis: Boivin, T. L. Tetrahedron 1987, 43, 3309. Koert, U. Synthesis 1995, 115.
7. Review: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
8. Reviews: Hoppe, D. Angew. Chem. 1984, 96, 930; Angew. Chem., Int. Ed. Engl. 1984, 23, 932. Hoppe, D.; Krämer, T.; Schwark, J.-R.; Zschage, O. Pure Appl. Chem. 1990, 62, 1999.
9. Reviews: Hoppe, D. Angew. Chem. 1984, 96, 930; Angew. Chem., Int. Ed. Engl. 1984, 23, 932. Hoppe, D.; Krämer, T.; Schwark, J.-R.; Zschage, O. Pure Appl. Chem. 1990, 62, 1999.
10. Reviews: Hoppe, D. Angew. Chem. 1984, 96, 930; Angew. Chem., Int. Ed. Engl. 1984, 23, 932. Hoppe, D.; Krämer, T.; Schwark, J.-R.; Zschage, O. Pure Appl. Chem. 1990, 62, 1999.
11. Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis, 1996, 141.
12. Houben-Weyl, 4th ed.; Vol. VII, part 2a; Thieme: Stuttgart, 1975; p 239.
13. Narasaka, K.; Soai, K.; Aikawa, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1976, 49, 779.
14. In addition, a diastereomer of 14 was isolated with 2% yield.
15. -3, (using programs SHELX-86, SHELX-93, and SCHAKAL-92). Atomic coordinates, thermal parameters, bond lengths and angles, and FoFc-lists have been deposited at the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlichetechnische Information mbH, D-76344 Eggenstein-Leopoldshafen under deposition number CSD 404412.