Synthesis of 2-vinylcyclopentanols by SmI2/Pd(0)-promoted carbohydrate ring-contraction

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2857-2860

  Aurrecoechea, José M ^a   Löpez, Beatriz ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 VINYLCYCLOPENTANOL; CARBOHYDRATE; CYCLOPENTANONE DERIVATIVE; IODINE DERIVATIVE; PALLADIUM COMPLEX; PYRANOSIDE; SAMARIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

FELIS CATUS;

EID: 0032580421     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00317-7     Document Type: Article

References (35)

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26. 2 (ca 0.1 M in THF, 19 mL, 1.88 mmol) and the mixture was refluxed for 2.5 h. After cooling and aqueous work-up, purification by flash chromatography and HPLC afforded the diastereomeric vinylcyclopentanols.
27. 8. Examples of higher reactivity in galactopyranosides compared to the corresponding gluco-analogs have been previously observed: MiljKovic, M.; Yeagley, D.; Deslongchamps, P.; Dory, Y. L. J. Org. Chem. 1997, 62, 7597-7604. However, in the present case, the enhanced reactivity in the galacto-derivative is more likely related to the β-orientation of the MeO group that probably facilitates orbital overlap in the formation of intermediate 4 (Scheme 2).
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32. 10. The elimination of an adjacent alkoxy group from an organosamarium intermediate has recently been reported: Marco-Contelles, J.; Destabel, C.; Chiara, J. L. Tetrahedron-Asymmetry 1996, 7, 105-108.
33. 11. For examples of cyclic and acyclic transition structures in metalloallyl-aldehyde couplings see: (a) Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210-6223.
34. (b) Kadota, I.; Kawada, M.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1997, 62, 7439-7446.
35. 5d takes place at -30°C whereas ours are performed at 75°C. In comparison, substrate 1c affords, as mentioned above, increasing amounts of cis-products (vinyl and hydroxyl bearing carbons) when the reaction is carried out at lower temperatures, in line with the results reported in ref. 5d.