A stereospecific synthesis of 1,2-disubstituted homopropargylic protected alcohols from bromoallenols

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1649-1652

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

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; EPOXIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033605184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00078-7     Document Type: Article

References (24)

1. 1. Bernard, N; Chemla, F.; Normant, J. Tetrahedron Lett. 1998, 39, 8837-8840.
2. 2. For general references, see : Landor, S.R. Reactions of allenes. In The Chemistry of the Allenes; Landor, S.R. Ed; Academic Press: London, 1982; pp 241-244; Schuster, H.F.; Coppola, G.M. Allenes in Organic Synthesis; John Wiley&Sons: New York, 1984; pp 272-280.
3. 2. For general references, see : Landor, S.R. Reactions of allenes. In The Chemistry of the Allenes; Landor, S.R. Ed; Academic Press: London, 1982; pp 241-244; Schuster, H.F.; Coppola, G.M. Allenes in Organic Synthesis; John Wiley&Sons: New York, 1984; pp 272-280.
4. 3. Mavrov, M.V.; Voskanyan, E.S.; Kucherov, V.F. Tetrahedron 1969, 25, 3277-3285.
5. 4. Kalli, M.; Landor, P.D.; Landor, S.R. J; Chem. Soc., Perkin Trans. I 1973, 1347-1349.
6. 5. Caporusso, A.M.; Polizzi, C.; Lardicci, L. Tetrahedron Lett. 1987, 28, 6073-6076; Polizzi, C.; Consoloni, C.; Lardicci, L.; Caporusso, A.M. J. Organomet. Chem. 1991, 417, 289-304.
7. 5. Caporusso, A.M.; Polizzi, C.; Lardicci, L. Tetrahedron Lett. 1987, 28, 6073-6076; Polizzi, C.; Consoloni, C.; Lardicci, L.; Caporusso, A.M. J. Organomet. Chem. 1991, 417, 289-304.
8. 6. Corey, E.J.; Boaz, N.W. Tetrahedron Lett. 1984, 25, 3059-3062.
9. 7. Corey, E.J.; Kang, J. J. Am. Chem. Soc. 1981, 103, 4619-4620; Corey, E.J.; Pyne, S.G.; Schafer, A.I. Tetrahedron Lett. 1983, 24, 3291-3294; Corey, E.J.; De, B. J. Am. Chem. Soc. 1984, 106, 2735-2736; Bartlett, P.A.; Ting, P.C. J. Org. Chem. 1986, 57, 2230-2240.
10. 7. Corey, E.J.; Kang, J. J. Am. Chem. Soc. 1981, 103, 4619-4620; Corey, E.J.; Pyne, S.G.; Schafer, A.I. Tetrahedron Lett. 1983, 24, 3291-3294; Corey, E.J.; De, B. J. Am. Chem. Soc. 1984, 106, 2735-2736; Bartlett, P.A.; Ting, P.C. J. Org. Chem. 1986, 57, 2230-2240.
11. 7. Corey, E.J.; Kang, J. J. Am. Chem. Soc. 1981, 103, 4619-4620; Corey, E.J.; Pyne, S.G.; Schafer, A.I. Tetrahedron Lett. 1983, 24, 3291-3294; Corey, E.J.; De, B. J. Am. Chem. Soc. 1984, 106, 2735-2736; Bartlett, P.A.; Ting, P.C. J. Org. Chem. 1986, 57, 2230-2240.
12. 7. Corey, E.J.; Kang, J. J. Am. Chem. Soc. 1981, 103, 4619-4620; Corey, E.J.; Pyne, S.G.; Schafer, A.I. Tetrahedron Lett. 1983, 24, 3291-3294; Corey, E.J.; De, B. J. Am. Chem. Soc. 1984, 106, 2735-2736; Bartlett, P.A.; Ting, P.C. J. Org. Chem. 1986, 57, 2230-2240.
13. 8. Westmijze, H.; Vermeer, P. Synthesis 1979, 390-392.
14. 9. Oostveen, J.M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1980, 45, 1158-1160; Caporusso, A.M.; Polizzi, C.; Lardicci, L. J. Org. Chem. 1987, 52, 3920-3923.
15. 9. Oostveen, J.M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1980, 45, 1158-1160; Caporusso, A.M.; Polizzi, C.; Lardicci, L. J. Org. Chem. 1987, 52, 3920-3923.
16. 10. Corey, E.J.; Boaz, N.W. Tetrahedron Lett. 1984, 25, 3053-3066.
17. 11. D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C.-G. Tetrahedron Lett. 1994, 35, 7775-7778; D'Aniello,F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870-4871; D'Aniello, F.; Mann, A.; Schoenfeldre, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636; D'Aniello, F.; Mann, A.; Schoenfeldre, A.; Taddei, M. Tetrahedron 1997, 53, 1447-1456.
18. 11. D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C.-G. Tetrahedron Lett. 1994, 35, 7775-7778; D'Aniello,F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870-4871; D'Aniello, F.; Mann, A.; Schoenfeldre, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636; D'Aniello, F.; Mann, A.; Schoenfeldre, A.; Taddei, M. Tetrahedron 1997, 53, 1447-1456.
19. 11. D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C.-G. Tetrahedron Lett. 1994, 35, 7775-7778; D'Aniello,F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870-4871; D'Aniello, F.; Mann, A.; Schoenfeldre, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636; D'Aniello, F.; Mann, A.; Schoenfeldre, A.; Taddei, M. Tetrahedron 1997, 53, 1447-1456.
20. 11. D'Aniello, F.; Mann, A.; Taddei, M.; Wermuth, C.-G. Tetrahedron Lett. 1994, 35, 7775-7778; D'Aniello,F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870-4871; D'Aniello, F.; Mann, A.; Schoenfeldre, A.; Taddei, M. J. Org. Chem. 1996, 61, 9631-9636; D'Aniello, F.; Mann, A.; Schoenfeldre, A.; Taddei, M. Tetrahedron 1997, 53, 1447-1456.
21. 12. Bernard, N; Chemla, F.; Normant, J. Tetrahedron Lett. 1998, 39, 6715-6718.
22. 13. Caporusso, A.M.; Da Settimo, F.; Lardicci, L. Tetrahedron Lett. 1985, 26, 5101-5104.
23. 14. Magid, R.M. Tetrahedron 1980, 36, 1901-1930. To the best of our knowledge, only one example of substitution reaction of haloallenes with Grignard reagents is reported in the litterature, with a low regioselectivity : Bargar, T.M.; Lett, R.M.; Johnson, P.L.; Hunter, J.E.; Chang, C.P.; Pernich, D.J.; Sabol, M.R.; Dick, M.R. J. Agric. Food Chem. 1995, 43, 1044-1051.
24. 14. Magid, R.M. Tetrahedron 1980, 36, 1901-1930. To the best of our knowledge, only one example of substitution reaction of haloallenes with Grignard reagents is reported in the litterature, with a low regioselectivity : Bargar, T.M.; Lett, R.M.; Johnson, P.L.; Hunter, J.E.; Chang, C.P.; Pernich, D.J.; Sabol, M.R.; Dick, M.R. J. Agric. Food Chem. 1995, 43, 1044-1051.