Diastereoselective carbometalation of δ-mono and γ-δ-bisubstituted Z vinyl metals

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5873-5876

  Bähr, Anja ^a   Marek, Ilane ^a   Normant, Jean F ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATE; METAL DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHELATION; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030581415     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01251-8     Document Type: Article

References (16)

1. 1. a) Bartlett, P. A. Tetrahedron 1980, 36, 2-72.
2. b) Ager, D. J. ; East, M. B. Tetrahedron 1993, 49, 5683-5765.
3. 2. a) Knochel, P. In comprehensive organic Synthesis ; Trost, B. ; Fleming, I., Eds Pergamon Press, New York, 1991, Vol 4, 865-911.
4. b) Klein, S. ; Marek, I. ; Poisson J.F. ; Normant, J.F. J. Am. Chem. Soc. 1995, 117, 8853-8854 and references cited therein.
5. 3. a) Brasseur D. ; Marek, I. ; Normant, J.F. Tetrahedron 1996, 52, 7235-7250.
6. b) Marek, I. ; Beruben, D. ; Normant, J.F. Tetrahedron Lett. 1995, 36, 3695-3698.
7. c) Wang, F. ; Marek, I. ; Labaudinière, L. ; Jie, J. ; Normant, J.F. Synlett 1995, 723-725.
8. d) Beruben, D. ; Marek, I. ; Normant, J.F. ; Platzer, N. J. Org. Chem. 1995, 60, 2488-2501.
9. 4. Alexakis, A. ; Duffault, J.M. Tetrahedron Lett. 1988, 29, 6243-6246.
10. 5. Marek, I. ; Lefrançois, J.M. ; Normant, J.F. Bull. Soc. Chim. Fr. 1994, 131, 910-918.
11. 6. a). Marek, I. ; Lefrançois, J.M. ; Normant, J.F. J. Org. Chem. 1994, 59, 4154-4166.
12. b). The stereochemistry of 4 and 5 were determined after iodocyclization of the olefinic tButyl ether. Marek, I.; Lefrançois, J.M.; Normant, J.F. Tetrahedron Lett. 1992, 33, 1747-1748.
13. 7. The preparation of each pure diastereomer and the determination of the structure of all iodo methyl tetrahydropyrans will be reported in due course.
14. 8. During the halogen-exchange step, the formation of ∼ 30% of alkyne was identified. This side product arose from an elimination process either via β or α-metalation of 6. This reaction was already pointed out in the litterature. Suffert, J. ; Toussaint, D. J. Org. Chem. 1995, 60, 3550-3551.
15. 9. Auerbach, J.; Weinreb, S.M. J. Chem. Soc., Chem. Commun. 1974, 298-299.
16. 2-I position