Stereoselective Intramolecular [4 + 3] Cycloadditions of Nitrogen-Stabilized Chiral Oxyallyl Cations via Epoxidation of N-Tethered Allenamides

Journal of the American Chemical Society

Volumn 125, Issue 42, 2003, Pages 12694-12695

  Xiong, Hui ^a   Huang, Jian ^a   Ghosh, Sunil K ^a   Hsung, Richard P ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENAMIDE; CATION; DIMETHYLDIOXIRANE; FURAN; HETEROCYCLIC AMINE; IODIDE; NITROGEN; OXAZOLIDINONE DERIVATIVE; OXYALLYL CATION; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; EPOXIDATION; REACTION ANALYSIS; REPRODUCIBILITY; RING OPENING; STEREOCHEMISTRY;

EID: 0142135994     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030416n     Document Type: Article

References (39)

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37. 20D, and MS.
38. This is the first time we observed such epoxidation of [4 + 3] cycloadducts in the presence of DMDO. The major isomer is shown as drawn with its stereochemistry being assigned via nOe.
39. Method B was not useful in these cases even with the reaction being run at a concentration of 0.0023 M and using ≥ 10 equiv of DMDO.