Lithium-liquid ammonia mediated carbocyclisation of δ,ε- unsaturated esters: Annulation of cyclopentanones

Tetrahedron Letters

Volumn 45, Issue 2, 2004, Pages 379-382

  Srikrishna, A ^a   Ramasastry, S S V ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Carbanion cyclisation; Cyclopentane annulation; Lithium in liquid ammonia

Indexed keywords

AMMONIA; CYCLOPENTANONE DERIVATIVE; ESTER DERIVATIVE; LITHIUM;

ANNULATION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CYCLIZATION; LIQUID; OXIDATION; REACTION ANALYSIS; SEPARATION TECHNIQUE; STRUCTURE ANALYSIS;

EID: 0346366641     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.164     Document Type: Article

References (17)

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7. To the best of our knowledge there is only one report on the intramolecular addition of esters to olefins under alkali metal in liquid ammonia conditions assisted by an α-hydroxy group (claimed as radical anion mediated addition), see: Cossy J., Gille B., Bellosta V. J. Org. Chem. 63:1998;3141-3146.
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9. ++Na+1): Calcd 190.1333. Found 190.1331.
10. For 8a : Eilbracht P., Acker N., Haedrich I. Chem. Ber. 121:1988;519. for 8b : Wender P.A., White A.W. J. Am. Chem. Soc. 110:1988;2218. for 8e : Dygutsch D.P., Eilbracht P. Tetrahedron. 52:1996;5461. for 8f : Chavan S.P., Patil S.S., Ravindranathan T. Tetrahedron. 55:1999;13417. for 8i : Jung M.E., Johnson T.W. Tetrahedron. 57:2001;1449. for 8l : Majerski Z., Hamersak Z. J. Org. Chem. 49:1984;1182.
11. For 8a : Eilbracht P., Acker N., Haedrich I. Chem. Ber. 121:1988;519. for 8b : Wender P.A., White A.W. J. Am. Chem. Soc. 110:1988;2218. for 8e : Dygutsch D.P., Eilbracht P. Tetrahedron. 52:1996;5461. for 8f : Chavan S.P., Patil S.S., Ravindranathan T. Tetrahedron. 55:1999;13417. for 8i : Jung M.E., Johnson T.W. Tetrahedron. 57:2001;1449. for 8l : Majerski Z., Hamersak Z. J. Org. Chem. 49:1984;1182.
12. For 8a : Eilbracht P., Acker N., Haedrich I. Chem. Ber. 121:1988;519. for 8b : Wender P.A., White A.W. J. Am. Chem. Soc. 110:1988;2218. for 8e : Dygutsch D.P., Eilbracht P. Tetrahedron. 52:1996;5461. for 8f : Chavan S.P., Patil S.S., Ravindranathan T. Tetrahedron. 55:1999;13417. for 8i : Jung M.E., Johnson T.W. Tetrahedron. 57:2001;1449. for 8l : Majerski Z., Hamersak Z. J. Org. Chem. 49:1984;1182.
13. For 8a : Eilbracht P., Acker N., Haedrich I. Chem. Ber. 121:1988;519. for 8b : Wender P.A., White A.W. J. Am. Chem. Soc. 110:1988;2218. for 8e : Dygutsch D.P., Eilbracht P. Tetrahedron. 52:1996;5461. for 8f : Chavan S.P., Patil S.S., Ravindranathan T. Tetrahedron. 55:1999;13417. for 8i : Jung M.E., Johnson T.W. Tetrahedron. 57:2001;1449. for 8l : Majerski Z., Hamersak Z. J. Org. Chem. 49:1984;1182.
14. For 8a : Eilbracht P., Acker N., Haedrich I. Chem. Ber. 121:1988;519. for 8b : Wender P.A., White A.W. J. Am. Chem. Soc. 110:1988;2218. for 8e : Dygutsch D.P., Eilbracht P. Tetrahedron. 52:1996;5461. for 8f : Chavan S.P., Patil S.S., Ravindranathan T. Tetrahedron. 55:1999;13417. for 8i : Jung M.E., Johnson T.W. Tetrahedron. 57:2001;1449. for 8l : Majerski Z., Hamersak Z. J. Org. Chem. 49:1984;1182.
15. For 8a : Eilbracht P., Acker N., Haedrich I. Chem. Ber. 121:1988;519. for 8b : Wender P.A., White A.W. J. Am. Chem. Soc. 110:1988;2218. for 8e : Dygutsch D.P., Eilbracht P. Tetrahedron. 52:1996;5461. for 8f : Chavan S.P., Patil S.S., Ravindranathan T. Tetrahedron. 55:1999;13417. for 8i : Jung M.E., Johnson T.W. Tetrahedron. 57:2001;1449. for 8l : Majerski Z., Hamersak Z. J. Org. Chem. 49:1984;1182.
16. In addition 16% of the corresponding aldehyde was also obtained.
17. In addition, the 6-endo cyclisation, a dominant reaction with the 5-substituted-5-hexenyl radicals, with δ-substituted esters was not observed, which also further supports the absence of a radical intermediate in these cyclisations. See: doi:10.1016/j.tetlet.2003.10.165 Srikrishna A., Kumar P.R., Ramasastry S.S.V. Tetrahedron Lett. 44:2003;0000.