Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions of Nitroalkenes. A Versatile Asymmetric Synthesis of Highly Functionalized Aminocyclopentanes

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7086-7087

  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: 0000223315     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9713215     Document Type: Article

References (27)

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4. (e) Cascade Reactions; Grigg, R., Ed.; Tetrahedron Symposium in Print No. 62, 1996; Vol. 52 (35).
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12. For a review of a 1,3-dipolar cycloaddition approach to substituted aminocyclopentanols see: Padwa, A.; Schoffstall, A. M. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, 1990; Vol. 2, pp 1-89.
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15. The stereostructural assignment of the endo(alkoxy)-derived product 5a″ was established by X-ray crystal structure analysis.
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18. Determined by chiral stationary phase HPLC, see Supporting Information for details.
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26. Epimeric ratios ranging from 3-20/1 have been obtained for this reaction. The epimerization of C(1) in 7c may proceed via an enamine from a dehydrogenation/reduction sequence due to the benzylic nature of the hydrogen at the C(9) position of the nitroso acetal.
27. Nitroso acetal 6d was unstable to alumina and silica gel chromatography and was used in the subsequent reaction without purification.