Enantioselective synthesis of fused cycloheptadienes by a tandem intramolecular cyclopropanation/cope rearrangement sequence

Journal of Organic Chemistry

Volumn 64, Issue 23, 1999, Pages 8501-8508

  Davies, Huw M L ^a   Doan, Brian D ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKADIENE; ALKENE; AZULENE DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033550304     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990888d     Document Type: Article

References (57)

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32. 1H NMR resonances of the lactone methylene. See the Supporting Information for full details. equation presented
33. The absolute stereochemistry for cyclopropane 3g was determined by conversion to iii and comparison to published results. The absolute stereochemistry of cyclopropane 3h was determined by conversion to isopropyl butyrolactone iv and comparison to published results. See the Supporting Information for full details. equation presented
34. Relative stereochemistry of cyclopropanes 8a,b was assigned by nOe spectral analysis. Similarities in enhancement between the two cyclopropyl protons and the styrenyl proton suggest the spacial distances are equal and therefore the protons are oriented cis on the cyclopropanes. The relative stereochemistry of 8c has been previously determined (see ref 26). equation presented
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