Metalation of 3-trimethylsilyl propargyl chloride: A stereoselective access to trans-propargylic oxiranes

Tetrahedron Letters

Volumn 40, Issue 1, 1999, Pages 75-78

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

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

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

EID: 0032889878     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)80023-3     Document Type: Article

References (17)

1. Bernard, N.; Chemla, F.; Normant, N. Tetrahedron Lett. 1998, 39. 6715.
2. Bernard, N.; Chemla, F.; Normant, N. Tetrahedron Lett. 1998, 39. under press.
3. See for example : Carlson, R.G.; Cox, W.W. J. Org. Chem. 1977, 42, 2382; Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J.F. Tetrahedron 1991, 47, 1677-1696.
4. See for example : Carlson, R.G.; Cox, W.W. J. Org. Chem. 1977, 42, 2382; Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J.F. Tetrahedron 1991, 47, 1677-1696.
5. Cao, G.-A.; Wang, Z.X.; Tu, Y.; Shi, Y. Tetrahedron Lett. 1998, 39, 4425 and ref. cited therein.
6. 2 and sp Carbon Centers, in: Comprehensive Organic Synthesis, Trost, B.M.; Fleming, I. eds. ; Pergamon Press: London, 1991; 3, pp 521-549.
7. Verkruijsse, H.D.; Brandsma, L. Synth Commun. 1990, 20, 3375; for an alternate preparation, see : Komarov, N.N.; Shostakovskii, M.F.; Astaf' eva, L.N.J. Gen. Chem. USSR 1961, 1963.
8. Verkruijsse, H.D.; Brandsma, L. Synth Commun. 1990, 20, 3375; for an alternate preparation, see : Komarov, N.N.; Shostakovskii, M.F.; Astaf' eva, L.N.J. Gen. Chem. USSR 1961, 1963.
9. For related preparation of epoxides and aziridines through condensation of propargylic ylides onto aldehydes or imines, see: Zhou, Z.L.; Huang, Y.Z.; Shi, L.L.; Hu. J. J. Org. Chem. 1992, 57, 6598; Li, A.H.; Zhou, Y.G.; Dai, L.X.; Hou. X.L.; Xia, L.J.; Lin, L. J. Org. Chem. 1998, 63, 4338.
10. For related preparation of epoxides and aziridines through condensation of propargylic ylides onto aldehydes or imines, see: Zhou, Z.L.; Huang, Y.Z.; Shi, L.L.; Hu. J. J. Org. Chem. 1992, 57, 6598; Li, A.H.; Zhou, Y.G.; Dai, L.X.; Hou. X.L.; Xia, L.J.; Lin, L. J. Org. Chem. 1998, 63, 4338.
11. Huber, R.S.; Jones, G.B. Tetrahedron Lett 1994, 35, 2655: Jones, G.B.; Huber, R.S.; Mathews, J.E. J. Chem. Soc., Chem. Commun. 1995, 1791; McPhee, M.M; Kerwin, S.M. J. Org. Chem. 1996, 61, 9385.
12. Huber, R.S.; Jones, G.B. Tetrahedron Lett 1994, 35, 2655: Jones, G.B.; Huber, R.S.; Mathews, J.E. J. Chem. Soc., Chem. Commun. 1995, 1791; McPhee, M.M; Kerwin, S.M. J. Org. Chem. 1996, 61, 9385.
13. Huber, R.S.; Jones, G.B. Tetrahedron Lett 1994, 35, 2655: Jones, G.B.; Huber, R.S.; Mathews, J.E. J. Chem. Soc., Chem. Commun. 1995, 1791; McPhee, M.M; Kerwin, S.M. J. Org. Chem. 1996, 61, 9385.
14. The same phenomenon has already been reported in the case of chloroallyl anions : Mallaiah, K.; Satyanarayana, J.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1993. 34, 3145.
15. Epzstein, R. The Formation and Transformations of Allenic and α-acetylenic Carbanions, in: Comprehensive Carbanion Chemistry, Buncel, E; Durst, T. eds ; Elsevier: Amsterdam, 1984; B, pp 107-175; Yamamoto, H. Propargyl and Allenyl Organometallics, in: Comprehensive Organic Synthesis, Trost, B.M., Fleming, I. eds. ; Pergamon Press: London, 1991; 2, pp 81-98.
16. Epzstein, R. The Formation and Transformations of Allenic and α-acetylenic Carbanions, in: Comprehensive Carbanion Chemistry, Buncel, E; Durst, T. eds ; Elsevier: Amsterdam, 1984; B, pp 107-175; Yamamoto, H. Propargyl and Allenyl Organometallics, in: Comprehensive Organic Synthesis, Trost, B.M., Fleming, I. eds. ; Pergamon Press: London, 1991; 2, pp 81-98.
17. For a related example of ring-closure of propargylic bromohydrins, see :Kanger, T.; Niidas, P.; Müürisepp, A.; Pekh, T.; Lopp, M. Tetrahedron: Assym. 1998, 9, 2499.