Lewis acid-mediated ring opening of propargylic epoxides: A stereospecific synthesis of 1,2-disubstituted homopropargylic alcohols

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6715-6718

  Bernard, Nicolas ^a   Chemla, Fabrice ^a   Normant, Jean F ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE; EPOXIDE; PROPARGYLIC EPOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0032505237     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01433-6     Document Type: Article

References (23)

1. 1. Bähr, A.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1996, 37, 5873-5876.
2. 2. Yamamoto, H. Propargyl and Allenyl Organometallics, in: Comprehensive Organic Synthesis, Trost, Fleming eds. ; Pergamon Press: London, 1991; pp 81-98.
3. 3. Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4567. Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 11377-11390.
4. 3. Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4567. Harada, T.; Katsuhira, T.; Osada, A.; Iwazaki, K.; Maejima, K.; Oku, A. J. Am. Chem. Soc. 1996, 118, 11377-11390.
5. 4. Marshall, J.A.; Wang, X. J. Org. Chem. 1990, 55, 6246-6248; Marshall, J.A.; Wang, X. J. Org. Chem. 1992, 57, 1242-1252; Marshall, J.A.; Perkins, J. J. Org. Chem. 1994, 59, 3509-3511.
6. 4. Marshall, J.A.; Wang, X. J. Org. Chem. 1990, 55, 6246-6248; Marshall, J.A.; Wang, X. J. Org. Chem. 1992, 57, 1242-1252; Marshall, J.A.; Perkins, J. J. Org. Chem. 1994, 59, 3509-3511.
7. 4. Marshall, J.A.; Wang, X. J. Org. Chem. 1990, 55, 6246-6248; Marshall, J.A.; Wang, X. J. Org. Chem. 1992, 57, 1242-1252; Marshall, J.A.; Perkins, J. J. Org. Chem. 1994, 59, 3509-3511.
8. 5. Alexakis, A. Pure & Appl. Chem. 1992, 64, 387-392; Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J.F. Tetrahedron 1991, 47, 1677-1696.
9. 5. Alexakis, A. Pure & Appl. Chem. 1992, 64, 387-392; Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J.F. Tetrahedron 1991, 47, 1677-1696.
10. 6. Ortiz de Montellano, P.R. J. Chem. Soc., Chem. Commun. 1973, 709-710; Vermeer, P.; Meijer, J.; deGraaf, C.; Scheurs, H. Recl. Trav. Chim. Pays-Bas 1974, 93, 46; Tigchelaar, M.; Meijer, J.; Kleijn, H.; Bos, H.J.T.; Vermeer, P. J. Organomet. Chem. 1981, 221, 117-221; Oehlschlager, A.C.; Czyzewska, E. Tetrahedron Lett. 1983, 24, 5587-5590; Doutheau, A.; Sartoretti, J.; Goré, J. Tetrahedron 1983 39, 3059-3065; Marshall, J.A.; Pinney, K.G. J. Org. Chem. 1993, 58, 7180-7184.
11. 6. Ortiz de Montellano, P.R. J. Chem. Soc., Chem. Commun. 1973, 709-710; Vermeer, P.; Meijer, J.; deGraaf, C.; Scheurs, H. Recl. Trav. Chim. Pays-Bas 1974, 93, 46; Tigchelaar, M.; Meijer, J.; Kleijn, H.; Bos, H.J.T.; Vermeer, P. J. Organomet. Chem. 1981, 221, 117-221; Oehlschlager, A.C.; Czyzewska, E. Tetrahedron Lett. 1983, 24, 5587-5590; Doutheau, A.; Sartoretti, J.; Goré, J. Tetrahedron 1983 39, 3059-3065; Marshall, J.A.; Pinney, K.G. J. Org. Chem. 1993, 58, 7180-7184.
12. 6. Ortiz de Montellano, P.R. J. Chem. Soc., Chem. Commun. 1973, 709-710; Vermeer, P.; Meijer, J.; deGraaf, C.; Scheurs, H. Recl. Trav. Chim. Pays-Bas 1974, 93, 46; Tigchelaar, M.; Meijer, J.; Kleijn, H.; Bos, H.J.T.; Vermeer, P. J. Organomet. Chem. 1981, 221, 117-221; Oehlschlager, A.C.; Czyzewska, E. Tetrahedron Lett. 1983, 24, 5587-5590; Doutheau, A.; Sartoretti, J.; Goré, J. Tetrahedron 1983 39, 3059-3065; Marshall, J.A.; Pinney, K.G. J. Org. Chem. 1993, 58, 7180-7184.
13. 6. Ortiz de Montellano, P.R. J. Chem. Soc., Chem. Commun. 1973, 709-710; Vermeer, P.; Meijer, J.; deGraaf, C.; Scheurs, H. Recl. Trav. Chim. Pays-Bas 1974, 93, 46; Tigchelaar, M.; Meijer, J.; Kleijn, H.; Bos, H.J.T.; Vermeer, P. J. Organomet. Chem. 1981, 221, 117-221; Oehlschlager, A.C.; Czyzewska, E. Tetrahedron Lett. 1983, 24, 5587-5590; Doutheau, A.; Sartoretti, J.; Goré, J. Tetrahedron 1983 39, 3059-3065; Marshall, J.A.; Pinney, K.G. J. Org. Chem. 1993, 58, 7180-7184.
14. 6. Ortiz de Montellano, P.R. J. Chem. Soc., Chem. Commun. 1973, 709-710; Vermeer, P.; Meijer, J.; deGraaf, C.; Scheurs, H. Recl. Trav. Chim. Pays-Bas 1974, 93, 46; Tigchelaar, M.; Meijer, J.; Kleijn, H.; Bos, H.J.T.; Vermeer, P. J. Organomet. Chem. 1981, 221, 117-221; Oehlschlager, A.C.; Czyzewska, E. Tetrahedron Lett. 1983, 24, 5587-5590; Doutheau, A.; Sartoretti, J.; Goré, J. Tetrahedron 1983 39, 3059-3065; Marshall, J.A.; Pinney, K.G. J. Org. Chem. 1993, 58, 7180-7184.
15. 6. Ortiz de Montellano, P.R. J. Chem. Soc., Chem. Commun. 1973, 709-710; Vermeer, P.; Meijer, J.; deGraaf, C.; Scheurs, H. Recl. Trav. Chim. Pays-Bas 1974, 93, 46; Tigchelaar, M.; Meijer, J.; Kleijn, H.; Bos, H.J.T.; Vermeer, P. J. Organomet. Chem. 1981, 221, 117-221; Oehlschlager, A.C.; Czyzewska, E. Tetrahedron Lett. 1983, 24, 5587-5590; Doutheau, A.; Sartoretti, J.; Goré, J. Tetrahedron 1983 39, 3059-3065; Marshall, J.A.; Pinney, K.G. J. Org. Chem. 1993, 58, 7180-7184.
16. 7. Kleijn, H.; Meijer, J.; Overbeek, G.C.; Vermeer, P. Recl. Trav. Chim. Pays-Bas 1982, 101, 97-101.
17. 8. Trost, B.M.; Tour, J.M. J. Org. Chem. 1989, 54, 484-486.
18. 9. Perveev, F.Y.; Kudryashova, N.I. Zhur. Obshch. Khim. 1953, 23, 348-351; Chem. Abstr. 1954, 48, 2566d.
19. 9. Perveev, F.Y.; Kudryashova, N.I. Zhur. Obshch. Khim. 1953, 23, 348-351; Chem. Abstr. 1954, 48, 2566d.
20. 10. Krause, N.; Seebach, D. Chem. Ber. 1988, 121, 1315-1320.
21. 11. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391-394; Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693-3694.
22. 11. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391-394; Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693-3694.
23. 12. Hoffmann, R.W.; Giesen, V.; Fuest, M. J. Liebigs. Ann. Chem. 1993, 629-639.