Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions of Nitroalkenes. the Bridged Mode (β-Tether)

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6167-6177

  Denmark, Scott E ^a   Dixon, Julie A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001113253     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9802168     Document Type: Article

References (50)

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19. For a review of a 1,3-dipolar cycloaddition approach to substitued aminocyclopentanols see: Padwa, A.; Schoffstall, A. M. In Advances in Cycloadditions; Curran, D. P., Ed.; JAI Press: Greenwich 1990; Vol. 2, pp 1-89.
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33. The nitroalkene and vinyl ether are presumed to retain their stereochemical integrity under the reaction condition.
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36. This was subsequently confirmed by correlation of the end product 17 to an identical material derived from a nitroso acetal related to 14c whose structure was established by X-ray crystallography, see accompanying paper in this issue and Denmark, S. E.; Swiss, K. A.; Dixon, J. D. Acta Crystallogr. C 1996, C52, 2561.
37. 3 in [3 + 2] cycloadditions was critical for the success of these reactions, since the resulting nitroso acetals are acid labile.
38. Additionally, the use of lithium aluminum hydride as a reducing agent was explored but the starting nitroso acetal remained unchanged even in a refluxing solution of THF.
39. 2 promotes endo selective [4 + 2] cycloadditions and the relative chemical shift of the C(4) proton in the nitronate as discussed above.
40. The identity of 21 was secured by 1-D and 2-D NMR spectroscopy as well as other analytical techniques.
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42. 4 has never been addressed.
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48. X-ray crystal structure analysis of several chiral nitroso acetals from the β-tether tandem process indicate that the oxygen substituent prefers to be axial so that anomeric stabilization is gained, cf. ref 16.
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