Intramolecular trapping of esters and amides by 1-lithio-1- bromocyclopropanes

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 9081-9084

  Baird, Mark S ^a   Huber, Florian A M ^a   Tverezovzky, Viacheslav V ^b   Bolesov, Ivan G ^b  

^a BANGOR UNIVERSITY   (United Kingdom)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BICYCLO COMPOUND; BROMINE DERIVATIVE; CYCLOPROPANE DERIVATIVE; ESTER DERIVATIVE; HEXANOL; LITHIUM DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; MOLECULAR INTERACTION;

EID: 0032481075     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01999-6     Document Type: Article

References (16)

1. 1. For collected references see J. Bakkes, U.H. Brinker, Cyclopropylidene in Methoden der Organischen Chemie, Houbel-Weyl, Verlag Stuttgart, E19b, 1989, 391.
2. 2. N.O. Nilsen, L. Skattebol, M.S. Baird, S.R. Buxton and P.D. Slowey, Tetrahedron Lett., 1984, 2887.
3. 16
4. C 15.2, 21.9, 23.8, 28.1, 47.4, 70.8, 104.5.
5. 5. C. Berrier, B. Bonnaud, J.F. Patoiseau, D. Bigg, Tetrahedron, 1991, 46, 9629.
6. 6. A single isomer was isolated in each case after chromatography; minor signals in the crude mixture could not be assigned with certainty to a second isomer. The stereochemistry of (2f) was established by an n.O.e. study which showed a 2.5 % enhancement for the endo-H-6 when the signal for the 2-methyl group was irradiated (thanks are due to Dr. I.H. Sadler and the Edinburgh EPSRC High Field n.m.r. service for this determination). Other stereochemistries are assigned by analogy with this.
7. 7. Y. Gaoni, Tetrahedron Lett., 1983, 2833.
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9. C 23.2, 29.8, 42.3, 43.2, 67.2, 69.7, 199.3.
10. 10. M.T. Nunez, V.S. Martin, J.Org.Chem., 1990, 55, 1928.
11. 3).
12. C 23.4, 24.6, 34.2, 50.8, 52.1, 75.5, 127.0, 127.5, 128.5, 137.8, 154.1.
13. 13. Y. Li and T.J. Marks, J.Am.Chem. Soc., 1996, 118, 9295.
14. 14. M.S. Baird, P. Licence, V.V. Tverezovsky, I.G. Bolesov, W. Clegg, submitted for publication.
15. 15. V.V. Tverezovsky, Y.K. Grishin, I.G. Bolesov, M.S. Baird, J.Org.Chem.USSR, 1997, 33, 924.
16. 16. V.V. Tverezovsky, M.S. Baird and I.G. Bolesov, Tetrahedron, 1997, 53, 14773.