Diastereoselective synthesis of heterosubstituted organogembismetallic reagents. Application to a new propargylmetalation reaction of vinyl metals

Tetrahedron

Volumn 52, Issue 21, 1996, Pages 7235-7250

  Brasseur, Denis ^a   Marek, Ilane ^a   Normant, Jean F ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; SILANE DERIVATIVE; SULFIDE;

CONFERENCE PAPER; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029877445     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00248-7     Document Type: Conference Paper

References (27)

1. (a). Marek, I.; Lefrançois, J.M.; Normant, J.F. Bull. Soc. Chim. Fr. 1994, 131, 910.
2. (b). Marek, I.; Lefrançois, J.M.; Normant, J.F. J. Org. Chem. 1994, 59, 4154.
3. (a). Wang, F.; Tang, J.; Labaudinière, L.; Marek, I.; Normant, J.F. Synlett, 1995, 723.
4. (b). For the case of benzylic organozinc bromide, see : Klein, S.; Marek, I.; Normant, J.F. J. Org. Chem. 1994, 59, 2925.
5. (c). For the case of norbornyl zinc reagents see : Dudder, R.; Eckhardt, M.; Furlong, M.; Knoess, P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415.
6. Beruhen, D.; Marek, I.; Normant, J.F.; Platzer, N. J. Org. Chem. 1995, 60, 2488.
7. (a). Hofstee, H.K.; Boersma, J.; Van der Marlen, J.D.; Van der Kerk, G.J.M. J. Organomet. Chem. 1978, 153, 245.
8. (b). Thiele, K.H.; Heinrich, M.; Brüser, W.; Schröder, S. Z. Anorg. Allg. Chem. 1911, 432, 221.
9. The kinetics of this rearrangement are strongly dependent on the chelation of the zinc atom (tert-butoxy ether, 3h at -30°C, methoxymethyl ether 3h at -20°C, alcoolate, 30h at -20°C), see ref 1. Moreover, the same reaction in a more basic solvent is slower : Knochel, P.; Normant, J.F. Tetrahedron Lett. 1986, 27, 1039, 1043, 4427, 4431, 5727.
10. Marek, I.; Beruhen, D.; Normant, J.F. Tetrahedron Lett., 1995, 36, 3695.
11. (a). Marek, I.; Meyer, C.; Normant, J.F. Org. Synth. 1995, In Press.
12. (b). Meyer, C.; Marek, I.; Normant, J.F. Synlett 1993, 386
13. (c). Marek, I.; Alexakis, A.; Normant, J.F. Tetrahedron Lett. 1991, 32, 5329.
14. (d). Ma, S.; Lu, X. J. Chem. Soc., Chem, Commun. 1990, 1643.
15. (e). Biougne, J.; Theron, F. C. R. Acad. Sc. Paris Serie C 1971, 272, 858.
16. (f). Carpita, A.; Neri, D.; Rossi, R. Gazz. Chem. Ital. 1987, 117, 481.
17. The relative configuration of 7syn, 7anti, 13,14,15,16 were attributed by analogy with our preceding study on the carbometalation reaction, see ref. 1.
18. The same diastereoselectivity was also obtained starting from an even stronger chelating amino derivative, such as 3-(N,N-dimethyl)-amino-1-iodo-pent-1(Z)-ene.
19. (a). Meyer, C.; Marek, L; Courtemanche, G.; Normant, J.F. J. Org. Chem. 1995, 60, 863.
20. (b). Lorthiois, E.; Marek, I.; Meyer, C.; Normant, J.F. Tetrahedron Lett. 1995, 36, 1263.
21. Meyer, C.; Marek, I.; Normant, J.F.; Platzer, N. Tetrahedron Lett. 1994, 35, 5645.
22. The propargyl metalation of alkynyl metals was already described, see Mesnard, D.; Miginiac, L. J. Organomet. Chem. 1991, 420, 163.
23. Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565.
24. The 1(Z)-magnesio-1-heptene was prepared by halogen-lithium exchange of the corresponding iodo derivative, followed by a transmetalation with 1 equiv of magnesium bromide.
25. On, H.P.; Lewis, W.; Zweifel, G. Synthesis 1981, 999.
26. Yamamoto, H. Comprehensive Organic Synthesis, Trost, B. ; Fleming, I., Eds., Pergamon Press, New York, 1991, 2, 81.
27. Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J.F. Tetrahedron, 1994, 50, 11665.