Thermal intramolecular [4 + 2] cycloadditions of allenamides: A stereoselective tandem propargyl amide isomerization-cycloaddition

Organic Letters

Volumn 11, Issue 15, 2009, Pages 3430-3433

  Lohse, Andrew G ^a   Hsung, Richard P ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMIDES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HETEROCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 68149092549     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901283m     Document Type: Article

References (48)

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38. 3 (in 10-100 mol % at rt to 65 °C) led to very low yields of possible cycloadduct (ii) with mostly hydrolysis of the starting allenamide and decomposition. Only when using AgSbF6 was a modest yield attained for cycloadduct ii.
39. See Supporting Information.
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43. In addition, the regioisomeric cycloadduct 23 was found to equilibrate to 22 via retro-[4 + 2] and [4 + 2] after heating at 110 °C in toluene for 22 h.
44. 4, we were able to isolate some products (iii and iv) that are related to those reported by Hashmi amd Echavarren (see ref 23).
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