Synthesis of 1-aryl-2-vinyl cyclopropanes by intramolecular carbolithiation

Tetrahedron Letters

Volumn 38, Issue 46, 1997, Pages 8085-8088

  Krief, Alain ^a   Couty, François ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0030825919     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10115-0     Document Type: Article

References (18)

1. Krief, A.; Barbeaux, P.; J. Chem. Soc. Chem. Commun. 1987, 1214-16.
2. (a) Review article on the carbocyclisation reaction : Knochel, P. In Comprehensive Organic Synthesis. Vol. 4, Trost, B.M.; Fleming, I. Eds. Pergamon Press: Oxford, 1991, pp 865-72.
3. (b) for selected recent examples : (i) Cooke, M.P.; Huang, J.J. Synlett, 1997, 535-36.
4. (ii) Lorthiois, E.; Marek, I.; Normant, J.F. Tetrahedron Lett. 1996, 37, 6693-94
5. (iii) Krief, A.; Kenda, B.; Maertens, C.; Remacle, B. Tetrahedron, 1996, 52, 7465-73
6. (iv) Krief, A.; Bousbaa, J. Synlett, 1996, 1007-09.
7. (a) Lansbury, P.T.; Caridi, F.J.; Chem. Commun. 1970, 714-15 and references cited therein. (b) for rare examples reporting stable α-cyclopropylalkyllithiums
8. (i) Maesker, A.; Roberts, J.D. J. Am. Chem. Soc. 1966, 88, 1742-45. (ii) our ref. 2b (ii).
9. (a) Krief, A.; Hobe, M. Tetrahedron Lett. 1992, 33, 6527-30
10. (b) Krief, A.; Hobe, M. Tetrahedron Lett. 1992, 33, 6529-32.
11. Clarembeau, M.; Krief, A. Tetrahedron Lett. 1985, 26, 1093-96.
12. N2' alkylation of 3.
13. For other examples of intramolecular carbolithiation-elimination see: (a) Broka, C.A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-84
14. (b) Bailey, W.F.; Zarcone, L.M. Tetrahedron Lett. 1991, 32, 4425-26
15. (c) Manabe, S.; Chem. Commun. 1997, 8, 737-38.
16. Kato, T.; Marumoto, Sato; Kuwajima, I. Synlett 1990, 671.
17. We have not been able to produce the (Z)-sulfonates since they decompose very rapidly. This is probably due to an intramolecular substitution of the sulfonate by the selenide placed in suitable position owing to the stereochemistry of the C,C double bond.
18. The synthesis of these compounds will be reported in the full paper.